Volume 29, Issue 1
Natural Products
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ChemInform Abstract: Synthesis and X-Ray Crystallographic Study of Cyclobis-(1→2)-α-D-glucopyranosyl Peracetate.

V. POZSGAY

V. POZSGAY

Lab. Dev. Mol. Immun., Natl. Inst. Child Health Human Dev., NIH, Bethesda, MD 20892, USA

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E. P. DUBOIS

E. P. DUBOIS

Lab. Dev. Mol. Immun., Natl. Inst. Child Health Human Dev., NIH, Bethesda, MD 20892, USA

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H. LOTTER

H. LOTTER

Lab. Dev. Mol. Immun., Natl. Inst. Child Health Human Dev., NIH, Bethesda, MD 20892, USA

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A. NESZMELYI

A. NESZMELYI

Lab. Dev. Mol. Immun., Natl. Inst. Child Health Human Dev., NIH, Bethesda, MD 20892, USA

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First published: 24 June 2010

Abstract

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ChemInform Abstract

A facile synthesis of title compound (VI), which is easily transformed to cyclokojibiose (VII), is achieved in excellent yield. Key step is the novel activated anomeric carbon atom-mediated debenzylation of (V), which proceeds with complete selectivity and gives (VI) as the single product. X-ray crystallographic studies of (VI) reveal, that the glucopyranosyl moieties are interconnected by a 1,4-dioxane moiety, which is in a boat conformation with the anomeric carbon atoms in the bow positions.

chemical structure image

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