Open AccessAutomated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives
Author(s) -
Mallory K. Kern,
Nicola L. B. Pohl
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01236
Subject(s) - chemistry , glycoside , hydrolysis , combinatorial chemistry , oligosaccharide , glycosylation , phase (matter) , enzymatic hydrolysis , carbohydrate , organic chemistry , stereochemistry , biochemistry
Thioglycosides are more resistant to enzymatic hydrolysis than their O-linked counterparts, thereby becoming attractive targets for carbohydrate-based therapeutic development. We report the first development of methods for the site-selective incorporation of S-linkages into automated solution-phase oligosaccharide protocols. The protocols were shown to be compatible with the formation of S - or O -glycosides for the synthesis of mannopyranoside trimmers that incorporate both S- and O-linkages to allow the selective incorporation of an S -glycoside in various stages in an automated program.