A concise synthesis of methyl 2,6-dideoxy-2-fluoro-beta-L-talopyranoside

Authors
Deal, ST Horton, D
Citation
St. Deal et D. Horton, A concise synthesis of methyl 2,6-dideoxy-2-fluoro-beta-L-talopyranoside, CARBOHY RES, 315(1-2), 1999, pp. 187-191
Citations number
22
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
315
Issue
1-2
Year of publication
1999
Pages
187 - 191
Database
ISI
SICI code
0008-6215(19990131)315:1-2<187:ACSOM2>2.0.ZU;2-E
Abstract
The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-alpha,beta-D-glucopyr anoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetra chloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-al pha-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resu ltant 5,6-ene gave the 5-epimer of 6, which after removal of the ester subs tituents, afforded the title compound in good overall yield. (C) 1999 Elsev ier Science Ltd. All rights reserved.