Open AccessSelective desulfonylation in D-xylofuranose 3,5-disulfonates
Author(s) -
Admir Hadžić,
S Nada Vukojevic
Publication year - 2001
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc0105289h
Subject(s) - sulfonyl , regioselectivity , chemistry , hydrolysis , alcohol , organic chemistry , catalysis , alkyl
A method for the preparation of D-xylofuranose derivatives with a free terminal (C5) alcohol function was developed, starting from monocyclohexylidene-3,5-disulfonyl- or 5-O-sulfonyl-3-O-methyl ester. The regioselective displacement of the C5 sulfonyl ester functionwith acetate ion in dimethylsulfoxide afforded the corresponding 5-O-acetyl-1,2-O-cyclohexylidene-3-O-sulfonyl or 5-O-acetyl-3-O-methyl- -D-xylofuranose. These esters could be readily hydrolysed into the desired 1,2,3-trisubstituted xylofuranose.