Patent ID: 6831164
Filing Date: 2004-12-14
Classification: C07H

Abstract:
A process for production of a peracylated 1-O-glycoside formula I in whichsugar1 is a monosaccharide that is functionalized in 1-OH-position by -L-X-H, R is methyl, ethyl, propyl, isopropyl, tert-butyl, or phenyl, n is 2, 3 or 4, X is â€”COOâ€” or â€”NHâ€”, and L is a straight-chain, branched, saturated or unsaturated C1-C30 carbon chain, wherein said carbon chain optionally contains 1-10 oxygen atoms, 1-3 sulfur atoms, 1-2 phenylene groups, 1-2 phenylenoxy groups, 1-2 phenylenedioxy groups, a thiophene radical, pyrimidine radical or pyridine radical, and/or wherein said carbon chain is optionally substituted by 1-3 phenyl groups, 1-3 carboxyl groups, 1-5 hydroxy groups, 1-5 Oâ€”C1-C7 alkyl groups, 1-3 amino groups, 1-3 CF3 groups or 1-10 fluorine atoms, or a salt thereof, said process comprising: reacting a peracylated 1-OH-sugar of formula II with an alkylating reagent of formula (III)Nu-L-Xâ€”Sgâ€ƒâ€ƒ(III), in which Nu is a nucleofuge and Sg is a protective group,in an organic solvent in the presence of a base and optionally a phase transfer catalyst at a temperature of 0-50Â° C., andcleaving off the protective group, and optionally converting the resultant reaction product into a salt.