Patent GB-1236287-A (GB)
Title: Furanosides, process for their manufacture and compositions containing them
IPC: C07H15/04
Filed: 1968-09-09
Abstract: 1,236,287. Furanosides. CIBA-GEIGY A.G. 9 Sept., 1968 [11 Sept., 1967; 2 July, 1968], No. 42799/68. Heading C2C. Y, 1968], Novel compounds of Formula (I) in which R 1  represents an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic radical, and R 2  represents hydrogen or the acyl radical of an organic carboxylic acid, and in which one of R 3  and R 5  represents a hydrogen atom or an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic radical, and the other an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic radical, and the salts of compounds having salt-forming groups, are prepared by reacting a 6-desoxy- D-xylohexofuranose of Formula (II) in which R<SP>0</SP> 1  represents a free hydroxyl group and R<SP>0</SP> 2  represents a free hydroxyl group or an acyloxy radical, in which acyl is the radical of an organic carboxylic acid, or R<SP>0</SP> 1  and R<SP>0</SP> 2  together represent the grouping of the formula -O-X-O-, in which X is an optionally substituted methylene group, with a compound of the formula R 1 -OH in the presence of an acid, or by reacting a 6-desoxy-D-xylohexofuranose of the Formula (II), in which R<SP>0</SP> 1  represents a reactive esterified hydroxyl group and R<SP>0</SP> 2  represents an acyloxy radical, in which acyl is the acyl residue of an organic carboxylic acid, with a compound of formula R 1 -OH in the presence of an acid acceptor, or by treating a 5,6-bis-desoxy-D-xylohexofuranoside of the Formula (III) in which Y represents a reductively eliminable group and Z represents the group R 5 O-, or in which Y and Z together represent an oxido group, in order to reductively eliminate the group Y or to split the epoxide grouping formed by Y and Z and, if desired, saturating an unsaturated aliphatic hydrocarbon radical in a resulting compound, and/or, if desired, converting an acyloxy radical in the 2-position in a resulting compound into a free hydroxyl group, and/or, if desired, converting a free hydroxyl group in the 2-position in a resulting compound into a hydroxyl group esterified by an organic carboxylic acid, and/or, if desired, converting a resulting compound having a salt-forming group into a salt or a resulting salt into the free compound, and/or, if desired, splitting a resulting anomer mixture into the individual anomers. Starting materials of Formulae (II) and (III) prepared in known manner. The preparation of the following specific starting materials and intermediates is disclosed in the examples: 1,2 - O - isopropylidene - 3,5 - di - O benzyl - 6 - desoxy - α - D - glucofuranose, 1,2 - O - isopropylidene - 3,5 - di - O - (4 - chlorobenzyl) - 6 - desoxy - α - D - glucofuranose, 1,2 - O - isopropylidene - 3 - O - benzyl - 5 - O - (4 - chlorobenzyl)- 6 - desozy - # - L - idofuranose, 1,2 - O - isopropylzdene - 3,5 - di - O - benzyl - 6 - desoxy - # - L- idofuranose, 1,2 - O isopropylidene - 3,5 - di- O benzyl - 6 - O - trityl - α - D - glucofuranose, 1,2 - O - isopropylidene - 3,5 - di - O - benzyl. α - D - glucofuranose, ethyl - 3,5 - di - O - benzyl- D - glucofuranoside and ethyl - 3,5 - di - O- benzyl - 6 - O (4 - methylphenylsulphonyl)- D - glucofuranoside. Pharmaceutical compositions having antiinflammatory and anti-allergic activity, for oral, parenteral or topical administration, comprise a compound of the invention together with a pharmaceutical carrier.