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Unexpected Anomeric Selectivity of a 1-C-Arylglycal Donor in Kdo Glycoside Synthesis

Author:
Qian, Yuxin, Feng, Jianhao, Parvez, Masood, Ling, Chang-Chun
Source:
Journal of organic chemistry 2012 v.77 no.1 pp. 96-107
ISSN:
1520-6904
Subject:
X-ray diffraction, alcohols, glycosides, glycosylation, moieties, organic chemistry, stereoselectivity
Abstract:
A novel class of 1-C-arylglycals was developed and subjected to N-iodosuccinimide-mediated glycosylations with alcohols. Unexpectedly, all reactions provided 2-iodo-β-d-ketopyranosides in high yields and excellent stereoselectivity. After removal of the 2-iodide by radical conditions, the aryl group was smoothly oxidized to provide the corresponding β-Kdo glycosides. A mechanism for the stereoselective formation of β-d-ketopyranosides was proposed, which was supported by evidence from X-ray crystallography.
Agid:
5498624