Premium
Regio‐ and stereoselective glycosylation of 2‐( o ‐dihydroxyborylbenzyl) thioglucoside and unprotected methyl glycosides
Author(s) -
Lam Sarah,
Hsu MeiYuan,
Wang ChengChung
Publication year - 2020
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201900475
Subject(s) - chemistry , stereoselectivity , glycosylation , acceptor , glycosyl donor , intramolecular force , moiety , boronic acid , glycosyl , glycoside , stereochemistry , organic chemistry , medicinal chemistry , catalysis , biochemistry , physics , condensed matter physics
A highly regio‐ and stereoselective glycosylation of a boronic acid‐containing thioglucoside and unprotected methyl glycosides is described. A boronic acid moiety was installed at the ortho ‐position of the 2‐ O ‐benzyl group of a thioglucosyl donor. This provides transient partial protection for the unprotected glycosyl acceptor upon condensation and concomitantly prearranged the acceptor with respect to the donor for the ensuing intramolecular glycosylation.