A STEREOSPECIFIC APPROACH TOWARDS THE SYNTHESIS OF 2-DEOXY ALPHA-GLYCOSIDE AND BETA-GLYCOSIDE BASED ON A 1,2-ETHYL (PHENYL) THIO GROUP MIGRATION

Authors
ZUURMOND HM VANDERKLEIN PAM VANDERMAREL GA VANBOOM JH
Citation
Hm. Zuurmond et al., A STEREOSPECIFIC APPROACH TOWARDS THE SYNTHESIS OF 2-DEOXY ALPHA-GLYCOSIDE AND BETA-GLYCOSIDE BASED ON A 1,2-ETHYL (PHENYL) THIO GROUP MIGRATION, Tetrahedron, 49(29), 1993, pp. 6501-6514
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
29
Year of publication
1993
Pages
6501 - 6514
Database
ISI
SICI code
0040-4020(1993)49:29<6501:ASATTS>2.0.ZU;2-O
Abstract
Iodonium ion (NIS/TfOH)-assisted glycosylation of a sugar acceptor wit h properly protected ethyl (phenyl) 2-O-phenoxythiocarbonyl 1-thio-bet a-D-gluco- or 1-thio-alpha-D-mannopyranoside donors gives the respecti ve 1,2-trans linked 2'-ethyl (phenyl) thio-2'-deoxy-alpha-D-manno- or beta-D-glucopyranosides.