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. 2008 Oct 2;10(19):4367-70.
doi: 10.1021/ol801833n. Epub 2008 Sep 3.

Direct and stereoselective synthesis of alpha-linked 2-deoxyglycosides

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Direct and stereoselective synthesis of alpha-linked 2-deoxyglycosides

Jin Park et al. Org Lett. .

Abstract

alpha-Linked 2-deoxyglycosides were conveniently obtained by employing a glycosyl donor having a participating ( S)-(phenylthiomethyl)benzyl moiety at C-6, whereas 2,6-dideoxy-alpha-glycosides could be prepared by BF 3.Et 2O-promoted activation of allyl glycosyl donors.

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Figures

Scheme 1
Scheme 1
Direct activation of a 2,6-dideoxy allyl glycoside.
Scheme 2
Scheme 2
Armed-disarmed glycosylation strategy.

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