Diastereoselective synthesis of beta-(3,4,6-tri-O-benzyl-2-deoxy-beta-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine

Authors
Lieberknecht, A Griesser, H Kramer, B Bravo, RD Colinas, PA Grigera, RJ
Citation
A. Lieberknecht et al., Diastereoselective synthesis of beta-(3,4,6-tri-O-benzyl-2-deoxy-beta-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine, TETRAHEDRON, 55(21), 1999, pp. 6475-6482
Citations number
50
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
21
Year of publication
1999
Pages
6475 - 6482
Database
ISI
SICI code
0040-4020(19990521)55:21<6475:DSOB>2.0.ZU;2-Q
Abstract
Key steps in the synthesis of beta-(3,4,6-tri-O-benzyl-2-deoxy-beta-D-galac topyranosyl)-N-tert-butoxycarbonyl-D-alanine are the Wittig reaction of 2-d eoxy-galactopyranosylphosphonium salt 2 and Garner aldehyde, as well as the subsequent diastereoselective hydrogenation of the olefinated sugar 3a,b. (C) 1999 Elsevier Science Ltd. All rights reserved.