Efficient stereoselective synthesis of alpha-C-glycopyranosides using 2,2 '-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70]

Authors
Gotanda, K Matsugi, M Suemura, M Ohira, C Sano, A Oka, M Kita, Y
Citation
K. Gotanda et al., Efficient stereoselective synthesis of alpha-C-glycopyranosides using 2,2 '-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70], TETRAHEDRON, 55(34), 1999, pp. 10315-10324
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
34
Year of publication
1999
Pages
10315 - 10324
Database
ISI
SICI code
0040-4020(19990820)55:34<10315:ESSOAU>2.0.ZU;2-C
Abstract
Efficient synthesis of alpha-C-glycopyranosides through a radical addition reaction using 2.2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70] as a n initiator under mild condition was developed. This method made it possibl e to completely control the stereocenter at the anomeric position and obtai n only the alpha-anomer in high yield compared with AIBN, Et3B, and photo i rradiation methods. (C) 1999 Elsevier Science Ltd. All rights reserved.