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ChemInform Abstract: Manipulation of Free Carbohydrates via Stannylene Acetals. Preparation of β-Per-O-acyl Derivatives of D-Mannose, L-Rhamnose, 6-O-Trityl-D-talose, and D-Lyxose.

✍ Scribed by G. HODOSI; P. KOVAC

Publisher: John Wiley and Sons
Year: 2010
Weight: 39 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199801232

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✦ Synopsis

Manipulation of Free Carbohydrates via Stannylene Acetals. Preparation of β-Per-O-acyl Derivatives of D-Mannose, L-Rhamnose, 6-O-Trityl-D-talose, and D-Lyxose.

-A simple and high-yielding method for the preparation of the title compounds (III), (V), (VII), and (IX) with an axial OH group at C-2 is described. It utilizes the property of unprotected carbohydrates to preferentially form 1,2-O-cis stannylene acetals when treated with Bu 2 SnO. Acetylation of these acetals generally proceeds with retention of configuration at the anomeric position. In the case of (VIII), however, a mixture of products is obtained, probably due to a reversible isomerization of a 1,2-acetal into a 2,3-acetal during the course of the reaction.

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