bluuebunny/crossref_metadata_2025_split huggingface dataset:
Stereospecific synthesis of partially protected 2‐azido‐2‐deoxy‐D‐glucosyl D‐myo‐inositol: Precursor of a potential insulin mimetic and membrane protein anchoring site
Authors: Verduyn R. , Elie C. J. J. , Dreef C. E. , van der Marel G. A. , van Boom J. H. 
Published: September 2010

AbstractRacemic and partially protected myo‐inositol derivative 5 was coupled stereospecifically with the 2‐azido‐2‐deoxy‐glucosyl trichloroacetimidate donor 8. Optical resolution of the thus obtained diastereoisomeric mixture of dimers by silica gel column chromatography, and further protective group manipulations, afforded the suitably protected title compound 14.
Conditions for modified fischer glycosidations with n‐pentenol and other alcohols
Authors: Konradsson Peter , Roberts Carmichael , Fraser‐Reid Bert 
Published: September 2010

AbstractVarious O‐glycosides were prepared directly from the corresponding aldoses by use of 3 molar equivalents of an alcohol with catalytic amounts of trifluoromethanesulfonic acid (triflic acid) in dimethyl sulfoxide.
Synthesis and properties of two pyrromethenium salts; one with a rigid Z‐syn structure and another with a rigid E‐anti structure
Authors: Koek J. H. , van der Hoef K. , Roodenburg L. , Lugtenburg J. , Fokkens R. 
Published: September 2010

Abstract1,3,7,9‐Tetramethyldipyrrolo[1,2‐c:2′,1′‐f]pyrimidinium methanesulphonate (1) and 2,3,5,6,8,8‐hexamethyl‐8H‐benzo[1,2‐b:4,5‐b']dipyrrolium methanesulphonate (2) have been prepared via simple reaction schemes. The first has a rigid Z‐syn pyrromethenium structure, the second a rigid E‐anti structure. The E‐anti compound has a larger λmax value, higher extinction, higher fluorescence intensity and larger Stokes shift than the corresponding Z‐syn compound. Mobile pyrromethenium salts do not show appreciable fluorescence. Both systems react rapidly with nucleophiles at the central carbon of the conjugated system to form colourless non‐fluorescent tricyclic pyrromethane systems. Upon intravenous injection into rats, the title compounds lead to rapid death, in contrast to a related purromethene‐BF2 complex, which is completely harmless upon intravenous injection.
Synthesis of serine analogues to be used as modified phospho acceptor sites in substrates of protein kinase C
Authors: Broxterman H. J. G. , Liskamp R. M. J. 
Published: September 2010

AbstractSerine and threonine analogues (compounds 2‐6) are readily accessible by reaction of the anion of N,N‐dibenzylglycine ethyl ester (1) with an appropriate carbonyl compound. These analogues will be incorporated into Protein Kinase C (PKC) substrates. The serine aldehyde derivative 7 was used for the preparation of the corresponding diethyl acetal 9. This compound was the starting material in the synthesis of the suicide precursor 8, featuring a reductive amination leading to 12 and a Lewis‐acid‐catalysed cyclization giving 8.
Shape effects in the conversion of ethanol to hydrocarbons over alkaline‐free synthesised ZSM‐5 and alumina ted silicalite‐1 crystals
Authors: Voogd P. , Sollie J. C. , Doelwijt A. , van Bekkum H. 
Published: September 2010

AbstractDiffusion effects on conversion rates and product distributions in the ethanol to gasoline reaction on zeolite H‐ZSM‐5 were investigated. A sample of large ZSM‐5 crystals (Si/Al47) having a narrow particle‐size distribution was hydrothermally synthesised in an alkaline‐free medium, applying ammonium cations. X‐ray data indicate considerably heterogeneous aluminium distribution throughout the large ZSM‐5 crystals.In the ethanol conversion, comparison with conventional small H‐ZSM‐5 crystallites revealed that compounds having small critical diameters predominated in the product mixture when using large crystals. This is caused by their high relative mobility in the ZSM‐5 channels. As to xylene and ethyltoluene formation, high para selectivities were found, especially at low contact times. Large ZSM‐5 crystals deactivate rather quickly, mostly within 24 hours, because of coke deposition on the outer crystal surface.Large silicalite‐1 crystals, subjected to a post‐synthesis treatment with AlCl3 at high temperatures, showed comparable shape effects in the ethanol conversion. Unexpectedly, deactivation rates are not dissimilar from those of directly synthesised H‐ZSM‐5.
Oxidative debromination in a binuclear copper (I) complex
Authors: Gelling O. J. , Feringa Ben L. 
Published: September 2010

AbstractThe binuclear copper (I) complex Cu2 (2,6‐BPB‐1‐Br)(BF4)21.8CH3CN (8) undergoes at 20°C with O2 a rapid oxidative arene debromination.
Synthesis of vitamin‐K derivatives with different lengths of the alkyl side chain
Authors: Liu Benli , Gu Lianquan , Zhang Jingling 
Published: September 2010

AbstractThe radical alkylation of 1,4‐naphthoquinone with various lengths of fatty acids [H(CH2)nCO2H] in the presence of (NH4)2S2O8 and AgNO3 was studied. A simple and effective method was found for the synthesis of vitamin‐K derivatives with different lengths of alkyl side chain. Two types of vitamin‐K derivatives were synthesized. The first type, 2‐alkyl‐1,4‐naphthoquinones, was synthesized by a single step of radical alkylation of 1,4‐naphthoquinone with different lengths of fatty acids. The second type, 2‐alkyl‐3‐methyl‐1,4‐naphthoquinones, was synthesized by radical alkylation of 2‐methyl‐ 1,4‐naphthoquinone using the same reaction as for the first type, or by radical methylation of the first type. Our results show that the former method is suitable for the synthesis of long‐side‐chain (n > 11; n, number of carbon atoms in chain of the fatty acid) vitamin‐K derivatives, whereas the latter method is better for the synthesis of short‐side‐chain (n < 11) vitamin‐K derivatives. The structures of these newly synthesized vitamin‐K derivatives were identified by UV, IR, 1H NMR and MS spectra.
Stereospecific conversion of a racemic pantoyl lactone to D‐(‐)‐pantoyl lactone through microbial oxidation and reduction reactions
Authors: Kataoka Michihiko , Shimizu Sakayu , Yamada Hideaki 
Published: September 2010

AbstractA novel enzymatic process for the synthesis of D‐(‐)‐pantoyl lactone from a racemic mixture of pantoyl lactone is described. The process involves two stereospecific enzymatic reactions, i.e., stereospecific oxidation of L‐(+)‐pantoyl lactone to ketopantoyl lactone by Nocardia asteroides and asymmetric reduction of ketopantoic acid, which is formed through the spontaneous hydrolysis of ketopantoyl lactone, to D‐(‐)‐pantoic acid by Agrobacterium radiobacter without any modification of the remaining D‐(‐)‐pantoyl lactone. With 80 mg/ml of racemic pantoyl lactone as the substrate, the amount of D‐(‐)‐pantoyl lactone synthesized reached 71.3 mg/ml (82.8% ee; molar conversion yield, 89.1%).
Asymmetric epoxidation of allyl alcohol derivatives by ω‐hydroxylase from Pseudomonas oleovorans
Authors: Fu Hong , Shen Gwo‐Jenn , Wong Chi‐Huey 
Published: September 2010

AbstractThis paper described the application of non‐heme monooxygenase system from Pseudomonas oleovorans to the syntheses of chiral 3‐(benzyloxy)‐, 3‐(allyloxy)‐, 3‐(butyloxy)‐ and 3‐(aryloxy)‐1,2‐epoxypropanes (6) from their corresponding allyl alcohol derivatives. The epoxides were determined to be R forms with good enantiomeric excess. The specificities of the enzymatic epoxidation of olefines and hydroxylation of the radical probe trans‐2‐phenyl‐1‐methylcyclopropane were discussed with regard to the reaction mechanism.
Lipophilic diaza crown ethers in supported liquid membranes; influence of pH on transport rates and membrane stability
Authors: Nijenhuis Wilma F. , Walhof Judith J. B. , Sudhölter Ernst J. R. , Reinhoudt David N. 
Published: September 2010

AbstractLipophilic diaza‐18‐crown‐6 derivatives are used to transport potassium cations through supported liquid membranes. The influence of the pH of the aqueous phases on the rate of transport and membrane stability has been studied. At pH values lower than 10, the flux is reduced significantly because the ionophores are protonated and leach out of the membrane phase. With these carriers, proton‐driven transport is possible. The length of the alkyl chain attached to the carrier has a pronounced effect on membrane stability. Carriers having two n‐pentyl chains leach out to the aqueous phases at pH 10, whereas carriers with two n‐decyl or n‐tetradecyl chains result in a stable membrane system. Model calculations show that di‐n‐decyldiaza‐18‐crown‐6 forms a 1:1 complex with potassium cations (K 3.1 · 106 l ṁ mol−1) in 2‐nitrophenyl n‐octyl ether (NPOE). The calculated diffusion coefficient of the complex in NPOE is the same as the diffusion coefficient of the dibenzo‐18‐crown‐6 potassium cation complex in NPOE (1.1 · 10−3 cm2·h−1). This means that the higher potassium fluxes for diaza crown ethers compared to dibenzo crown ethers are due to stronger complexation in the membrane phase with potassium cations. Very high carrier concentrations (and, therefore, very high fluxes) can be obtained using these lipophilic diaza crown ethers.
Synthesis and spectroscopic properties of 14‐, 15‐, 15′ ‐ and 14′ ‐monodeutero‐ and 15,15′ ‐dideuterospheroidenes
Authors: Gebhard R. , van Dijk J. T. M. , Boza M. V. T. J. , van der Hoef K. , Lugtenburg J. 
Published: September 2010

AbstractThe high‐yield synthesis of four mono‐ and one dideutero‐labelled spheroidene, the carotenoid bound in the reaction centre ofRhodobacter sphaeroides 2.4.1, is described. The all‐Eisomers (14′‐2H)‐, (15′‐2H)‐, (15‐2H), (14‐2H)‐ and (15,15′‐2H2)spheroidenes have been prepared in high purity with more than 95%2H incorporation from C2H3CN and/or Dibal‐2H. The spectroscopic properties of the labelled compounds are discussed; the mass spectra reveal that toluene elimination from spheroidene is restricted to a single location in the molecule.
Synthesis and Structure of [Me4N][Ni(dmise)2]2, the first Conductor based on the Ni(C3S4Se)2 system
Authors: Cornelissen Joost P. , Reefman Derk , Haasnoot Jaap G. , Spek Anthony L. , Reedijk Jan 
Published: September 2010

AbstractElectrochemical oxidation of [Bu4N][Ni(dmise)2] in the presence of Me4NPF6 yields [Me4N][Ni(dmise)2]2, the selenone derivative of the superconducting [Me4N][Ni(dmit)2]2. The X‐ray structure of [Me4N][Ni(dmise)2]2 reveals a non‐stacking arrangement of paired anions. The [Ni(dmise)2]2 diads are connected along the c‐axis via a short intermolecular Se…Se contact of 3.277(3) Å. Preliminary conductivity measurements show a room temperature conductivity of 20 S cm−1 with a metallic behavior down to 140 K, at which point a metalinsulator transition occurs.
An improved method for the N‐alkylation of benzotriazole and 1,2,4‐triazole
Authors: Katritzky Alan R. , Kuzmierkiewicz Wojciech , Greenhill John V. 
Published: September 2010

AbstractThe N‐alkylation of benzotriazole and 1,2,4‐triazole with alkyl halides proceeds efficiently in the presence of sodium hydroxide in N,N‐dimethylformamide (DMF).
A convenient synthesis of DNA fragments nitrogen‐15 labeled at the exocyclic cytosine amino group
Authors: Kellenbach E. R. , van den Elst H. , Boelens R. , van der Marel G. A. , van Boom J. H. , Kaptein R. 
Published: September 2010

AbstractA convenient method is described for the synthesis of oligodeoxynucleotides 15N labeled at the exocyclic amino group of cytosine. The 4‐triazolide derivative of deoxyuridine is used as a building block in the solid phase synthesis of the oligodeoxynucleotide. Deprotection and cleavage from the solid support is achieved by treatment with 15N labeled NH4OH. This treatment also substitutes the 4‐triazolide group of the deoxyuridine by an 15N labeled amino group to yield 4‐15N cytosine. The method was applied to a DNA fragment corresponding to a glucocorticoid response element. The oligomer was characterised by 1H‐15N coherence spectroscopy.
Synthesis of 5β‐methyl‐6‐demethoxythebaine and its Diels‐Alder reaction to 6α,14α‐ethenoisomorphinans and 6β,14β‐ethenomorphinans (Chemistry of Opium Alkaloids, Part XXXV
Authors: Woudenberg R. H. , Piet D. P. , Sinnema A. , Lie T. S. , Maat L. 
Published: September 2010

AbstractDeprotonation of 6‐demethoxythebaine (1) with butyllithium, followed by reaction of the anion with dimethyl sulfate, gave the non‐conjugated diene 4 as the major product and title compound 5β‐methyl‐6‐demethoxythebaine (5) only in low yield. Therefore, 5 was prepared from 5β‐methylthebaine (6), which was converted into 5β‐methylcodeinone (7) and then reduced to 5β‐methylcodeine (8). Mesylation of 8 yielded 6‐O‐mesyl‐5β‐methylcodeine (9). Reaction of 9 with lithium bromide gave 5β‐methyl‐bromocodide (10) as the major product, together with 5. When 10 was treated with potassium tert‐butoxide, the desired 5 was obtained in good yield. Short treatment of 10 gave the intermediate 8‐bromo‐5‐methyl‐desoxycodeine‐A (11), which reacted further to 5 after prolonged treatment.Diels‐Alder reaction of 5 with ethyl acrylate yielded two products, ethyl 6α,14α‐ethenoisomorphinan‐7α‐carboxylate 13 and ethyl 6β,14β‐ethenomorphinan‐8β‐carboxylate 14, due to β‐face and α‐face approach, respectively. Similarly, with 3‐buten‐2‐one as the dienophile, a mixture of 7α‐acetyl‐6α,l4α‐ethenoisomorphinan 15 and 8β‐acetyl‐6β,14β‐ethenomorphinan 16 was obtained. Diels‐Alder reaction of 5 with maleic anhydride, followed by esterification of the adducts, yielded dimethyl 6α,l4α‐ethenoisomorphinan‐7β,8β‐dicarboxylate 19 and dimethyl 60,140‐ethenomorphinan‐7β,8β‐dicarboxylate 20 in a 7 : 3 ratio. The results of the Diels‐Alder reaction are discussed in connection with the substituents in the 5β‐ and 6‐position.
Reductive cleavage of the carbon‐phosphorus bond with alkali metals. I. Cleavage of functionalised triphenylphosphines; formation of secondary and primary phosphines
Authors: Budzelaar Peter H. M. , van Doorn Johannes A. , Meijboom Nico 
Published: September 2010

AbstractThe reductive cleavage reaction of functionalised triphenylphosphines 1–34 with Na/NH3 and Li/THF depends strongly on the nature of the functionality and on the reducing agent. No reduction occurs with 11, 24, 30, 31 and 32 in Na/NH3. Compounds 3, 4, 5, 10, 12, 13, 15, 19, 23, 25, 26 and 27 cleave to give the secondary phosphide in high yield with Na/NH3, whereas 2, 7 and 9 give a high yield with Li/THF. Reduction occurs but cleavage is poor with 6, 7, 14, 29 and 34 and Na/NH3, or with 11 and Li/THF. Primary ortho‐functionalised phenyl phosphines are obtained by a double cleavage reduction from 2, 5, 12, 25, 26 and 27 with Na/NH3. This unprecedented reaction proceeds via the secondary phosphine, which is formed by protonation of the corresponding phosphide with NH3. It occurs when the aryl group contains a strongly electron‐donating substituent. Multiple cleavage of aryl groups with extended π systems occurs with 7 and 34 when they are made to react with Li/THF. Halogens are cleaved from the phenyl group (16, 17, 18, 28 and 33, with Na/NH,), whereas SCH, groups are converted to the corresponding mercapto group (20, 21 and 22). Birch reduction (2 and 10) can take place in NH, but not in the aprotic solvent THF; it occurs only when other reactions are slow. Sodium amide is obtained via reaction of 8 in Na/NH,. Restricted Hartree‐Fock calculations were carried out for a number of substituted phenylphosphines. From the correlation between the energies and coefficients of the LUMO (always an aryl π* orbital) and the experimental cleavage data, it was concluded that there are three requirements for successful cleavage. The LUMO energy should be neither too high (no reduction) nor too low (radical anion too stable) and, further, the coefficient of the LUMO on the carbon attached to phosphorus must be large.
Non‐linear optical and electro‐optical polymers
Authors: Staring Emiel G. J. 
Published: September 2010

AbstractIn this review, we present a general overview of organic molecules and materials for non‐linear optics, with emphasis on materials for frequency doubling and for the Pockels or electro‐optic effect. After a short introduction on the molecular basis of second‐order non‐linearity, we shall discuss the relevant materials aspects of three important classes of organic non‐linear optical materials: organic crystals, Langmuir‐Blodgett films and poled polymers. The latter class of materials is, in our opinion, the most versatile of these three. We shall present some representative and recent examples of various types of poled polymer materials, their synthesis and their non‐linear optical properties.
Substituent effects. 14. Anomalous dissociation constants in water‐organic solvent mixtures: Benzylammonium ions and related systems
Authors: Hoefnagel A. J. , de Vos R. H. , Wepster B. M. 
Published: September 2010

AbstractThermodynamic dissociation constants in various water‐organic solvent mixtures are given for benzylammonium, benzyldialkylammonium, and (2‐phenylethyl)ammonium ions. Deviations from the Hammett equation (Eqn. 1) are similar to those observed for carboxylic acids, but of opposite sign. The extended Hammett equation (Eqn. 3), containing the hydrophobic constant, π, yields good correlations. Derived secondary normal sigma values are exemplified.
Photochemistry of α‐bis(methoxyimino)alkanes
Authors: Stunnenberg Frank , Cerfontain Hans 
Published: September 2010

AbstractThe photochemistry of the α‐bis(methoxyimino)alkanes 1–5 and the, structurally related, conjugated dihydro(methoxyimino)isoxazoles 6 and 7 was studied. Triplet‐photosensitized irradiation of 1–7 leads only to stepwise E‐Z isomerization. Photostationary‐state (pss) ratios for 1,6 and 7 are reported for the various applied triplet sensitizers. Direct irradiation with 254 nm leads to both E‐Z isomerization (which is the dominant reaction) and formation of products resulting from initial N‐O homolysis of the excited singlet ππ* state. Mechanisms for the formation of the various products are proposed and the relative importance of the various steps is indicated and discussed. For the α‐bis(methoxyimino)alkanes 1 and 3, only the (E,Z)‐isomer undergoes N‐O homolysis. With the (methoxyimino)isoxazolines 6 and 7, only the exocyclic NO bond exhibits homolysis and not the strained endocyclic bond.
Carbodiimides as important intermediates in the reaction of isocyanates with carboxylic acids
Authors: Schotman A. H. M. , Mijs W. J. 
Published: September 2010

AbstractThe reaction between isocyanates and carboxylic acids is known to lead to amides. We have studied the mechanism of catalysis of this reaction by phospholene oxides.The reaction between phenyl isocyanates and benzoic acid was monitored under various conditions using High‐Pressure Liquid Chromatography. It was found that the catalyst reacts with the iso‐cyanate under formation of a carbodiimide. The carbodiimide reacts with the carboxylic acid to form amide and isocyanate via an N‐acylurea as intermediate. The catalyst is partly deactivated by the acid. The phospholene catalyst was only found effective in reactions with aromatic isocyanates.
Synthesis of two branched heptopyranoside‐ (L,D‐Hepp)‐containing trisaccharides of the inner‐core region ofCitrobacter PCM1487
Authors: Boons G. J. P. H. , Overhand M. , van der Marel G. A. , van Boom J. H. 
Published: September 2010

AbstractThe diastereogenic addition of (phenyldimethylsilyl)magnesium chloride to methyl 3‐O‐allyl‐2,4‐di‐O‐benzyl‐α‐D‐manno‐hexodialdo‐1,5‐pyranoside gave a L‐glycero‐D‐manno‐heptopyranoside (L,D‐Hepp) derivative having at C‐7 the phenyldimethylsilyl function as a hydroxy‐masking group. The L,D‐Hepp) derivative was converted into two acceptors which could be applied successfully for the preparation of the trisaccharides L‐α‐D‐Hepp)‐(1→3)‐O‐[L‐α‐D‐Hepp‐(1→7)]‐L‐α‐D‐Hepp/‐O‐Me20and α‐D‐Glcp‐(1→3)‐O‐[L‐α‐D‐Hepp‐(1→7)]‐L‐D‐Hepp‐O‐Me26.
Synthesis of (12,13‐13C2)retinal and (13,1413C2)retinal: A strategy to prepare multiple‐13C‐labeled conjugated systems
Authors: Groesbeek M. , Rood G. A. , Lugtenburg J. 
Published: September 2010

Abstract(12,13‐13C2)Retinal, (13,14‐13C2)retinal, (19‐13C)retinal and (20‐13C)retinal (1) were prepared in a simple fashion in high yield via a consecutive strategy. The key step is the reaction of a N‐methoxy‐N‐methylamide with an alkyllithium or a Grignard reagent. The preparation of the required N‐methoxy‐N‐methylamide is discussed. In this scheme, only three commercially available 13C‐labeled starting materials (ethyl bromoacetate, acetonitrile and methyl iodide) are sufficient to construct retinals with any possible combination of 13C labeling in the conjugated tail end. This strategy is applicable to the preparation of many other conjugated systems, such as retinoids, carotenoids and polyenes.
Synthesis of sparsomycin derivatives, addressing its binding to the large ribosomal subunit
Authors: van den Broek L. A. G. M. , Antonisse A. J. J. , Ottenheijm H. C. J. , Felix A. San , Lázaro E. , Ballesta J. P. G. , Lelieveld P. 
Published: September 2010

AbstractThe syntheses of compounds 14–19, 6‐methyluracilacryloyl derivatives, and 27–29, photoreactive aryl azide analogs of the antitumor antibiotic sparsomycin (1) are described. All of the modifications in the 6‐methyluracilacryloyl part of 1 were achieved by selective reduction or by selective N‐ and O‐methylation of 6 (Scheme 2). The key step in the synthetic scheme to the photo‐affinity analogs is the reaction of the chloromethyl sulfoxides 20 and 21 with the properly protected cystamine 22 in liquid ammonia, to give the sparsomycin N‐protected amines 23 and 24, respectively (Scheme 4). Subsequently, the photoreactive groups, viz. a p‐azidosalicylyl and a 4‐azido‐2‐nitrophenyl group, were coupled with these amines. For an evaluation of the biological activity of the compounds prepared, inhibition of protein biosynthesis in two cell‐free assays, cell‐growth inhibition of E. coli in liquid medium and inhibition of murine leukemia L1210 colony formation in soft agar were studied. All variations introduced in the “western A” fragment of 1 render the drug biologically inactive. Apparently, the uracil ring plays an important role in the interaction of sparsomycin with the ribosomal peptidyl transferase and its unmodified presence is crucial for displaying activity. The photoprobes, carrying modifications in the “eastern C” fragment of 1, do interact with the ribosome, but less effectively than sparsomycin itself.
Pressure effects as mechanistic probes for homolytic thermal cobaltcarbon bond cleavage of cobalamins
Authors: Gamelkoorn H. J. , de Bolster M. W. G. , Balt S. 
Published: September 2010

AbstractThe effect of pressure on the rates of anaerobic thermal homolytic scission of the CoC bond in alkylcobalamins (RB12, R = adenosyl, methyl and neopentyl) has been determined in different solvents of varying viscosities. Homolytic fission is compared to bond breaking using βH elimination (isopropylcobalamin in ethylene‐glycol + water mixtures) and heterolysis. These two mechanisms are characterized by a volume of activation that is close to zero, whereas homolysis shows a substantial positive value (18.5 cm3 ṁ mol−1 for AdoB12, 17.0 cm3 ṁ mol−1 for MeB12 and 7.9 cm3 ṁ mol−1 for neopentylB12, all in ethylene glycol) for this parameter. Consequently, pressure effects can be used, with caution, as mechanistic probes to identify CoC bond fission mechanisms for the reactions studied.
Reactions of β‐sultones and carbyl sulfates with nucleophiles
Authors: Bakker Bert H. , Schonk Ruud M. , Cerfontain Hans 
Published: September 2010

AbstractRing opening of the octane‐β‐sultones 1a‐c by methanol gives the β‐methoxyoctane‐sulfonic acids 2a‐c by SN2 substitution at C‐O with inversion of the configuration. Hydrolysis of cis‐ and trans‐4,5‐octanesultones 1a‐b under acidic conditions is stereospecific and leads to threo‐ [(RR,SS)‐4u] and erythro‐5‐hydroxy‐4‐octanesulfonic acid [(RS,SR)‐4u], respectively, by a similar SN2 reaction on the carbon of the CO bond. Hydrolysis of 4,5‐octanesultones 1a‐b with base proceeds by attack at the sulfur atom of the β‐sultone ring to provide 5‐hydroxy‐4‐octanesulfonates (4v) with retention. Reaction of carbyl sulfates 5a‐b with methanol gives the methyl esters of 5‐hydroxy‐4‐octanesulfonic acid 7a‐b in a stereospecific way with retention of configuration by attack of methanol at the sulfonate sulfur atom.