Differential reactivity of alpha- and beta-anomers of glycosyl accepters in glycosylations. A remote consequence of the endo-anomeric effect?

Authors
Magaud, D Dolmazon, R Anker, D Doutheau, A Dory, YL Deslongchamps, P
Citation
D. Magaud et al., Differential reactivity of alpha- and beta-anomers of glycosyl accepters in glycosylations. A remote consequence of the endo-anomeric effect?, ORG LETT, 2(15), 2000, pp. 2275-2277
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
15
Year of publication
2000
Pages
2275 - 2277
Database
ISI
SICI code
1523-7060(20000727)2:15<2275:DROAAB>2.0.ZU;2-P
Abstract
[GRAPHICS] When phenyl tri-O benzyl-1-thio-beta-D-galactopyranosid acid esters were co upled with a 1/1 mixture of alpha and beta 2,3 di-O-protected D-galactopyra nosiduronic acid esters, the beta-anomer proved to be more reactive, Data f rom theoretical calculations suggested that the enhanced reactivity of this anomer compared with the a one would be due to a stronger hydrogen bond of the C-4 OH with the ring oxygen.