Ontology highlight
ABSTRACT:
SUBMITTER: Boltje TJ
PROVIDER: S-EPMC3076600 | biostudies-literature | 2011 Jan
REPOSITORIES: biostudies-literature
Boltje Thomas J TJ Kim Jin-Hwan JH Park Jin J Boons Geert-Jan GJ
Organic letters 20101215 2
Activation of a glycosyl donor protected with a 2-O-(S)-(phenylthiomethyl)benzyl ether chiral auxiliary results in the formation of an anomeric β-sulfonium ion, which can be displaced with sugar alcohols to give corresponding α-glycosides. Sufficient deactivation of such glycosyl donors by electron-withdrawing protecting groups is, however, critical to avoid glycosylation of an oxacarbenium ion intermediate. The latter type of glycosylation pathway can also be suppressed by installing additional ...[more]