Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-beta-D-gluco- and galactopyranosides displaying a range of anomeric substituents

Authors
Osborn, HMI Brome, VA Harwood, LM Suthers, WG
Citation
Hmi. Osborn et al., Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-beta-D-gluco- and galactopyranosides displaying a range of anomeric substituents, CARBOHY RES, 332(2), 2001, pp. 157-166
Citations number
33
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
332
Issue
2
Year of publication
2001
Pages
157 - 166
Database
ISI
SICI code
0008-6215(20010518)332:2<157:RCAOO4>2.0.ZU;2-A
Abstract
The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-be nzylidene-beta -D-gluco- and galactopyranosides has been studied. Regiosele ctivity is achieved by forming the copper chelate of the 2,3-diol using eit her sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylati ng agent. (C) 2001 Elsevier Science Ltd. All rights reserved.