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Glycosidation of an ambident organic phosphoroselenothioate in the presence of a Lewis acid

✍ Scribed by Wiesława Kudelska

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 144 KB
Volume: 10
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(1999)10:3<259::aid-hc14>3.0.co;2-#

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✦ Synopsis

An ambident O,O-dialkylphosphorose-

lenothioate is glycosidated in the presence of boron trifluoride etherate to give both Se-and S-glycosyl-phosphoroselenothioates, the former predominating. The stereochemical course of this reaction depends on the kind of sugar substrates. By selective oxidation of the mixture of products, the Se-glycosyl derivative is isolated.

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