REGIOSELECTIVE LIPASE-CATALYZED ACYLATION OF 4,6-O-BENZYLIDENE-ALPHA-D-PYRANOSIDE AND 4,6-O-BENZYLIDENE-BETA-D-PYRANOSIDE DERIVATIVES DISPLAYING A RANGE OF ANOMERIC SUBSTITUENTS

Authors
GRIDLEY JJ HACKING AJ OSBORN HMI SPACKMAN DG
Citation
Jj. Gridley et al., REGIOSELECTIVE LIPASE-CATALYZED ACYLATION OF 4,6-O-BENZYLIDENE-ALPHA-D-PYRANOSIDE AND 4,6-O-BENZYLIDENE-BETA-D-PYRANOSIDE DERIVATIVES DISPLAYING A RANGE OF ANOMERIC SUBSTITUENTS, Tetrahedron, 54(49), 1998, pp. 14925-14946
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
49
Year of publication
1998
Pages
14925 - 14946
Database
ISI
SICI code
0040-4020(1998)54:49<14925:RLAO4>2.0.ZU;2-5
Abstract
The application of Lipase enzymes to effect regioselective C-3-O-acyla tion of 4,6-O-benzylidene-beta-D-gluco- and -galactopyranosides displa ying a range of anomeric substituents, and C-2-O- acylation of phenyl 4,6-O-benzylidene-alpha-D-glucopyranoside and ethyl 4,6-O-benzylidene- 1-thio-alpha-D-glucopyranoside is reported. In particular this method has allowed introduction of a variety of acyl protecting groups at the C-3 hydroxyl group of ethyl 4,6-O-benzylidene-1-thio-beta-D-glucopyra noside 11.(C) 1998 Elsevier Science Ltd. All rights reserved.