4.4 Article

First synthesis of 4a-carba-β-D-galactofuranose

Journal

TETRAHEDRON LETTERS
Volume 48, Issue 52, Pages 9073-9076

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.10.138

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The synthesis of 4a-carba-beta-D-galactofuranose is described starting from diacetone glucose. The key ring-closure step was carried out by metathesis to form a cyclopentene. Catalytic hydrogenation of the C=C double bond gave the galacto configured saturated carbahexofuranose with excellent diastereoselectivity. (C) 2007 Elsevier Ltd. All rights reserved.

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