Journal
TETRAHEDRON LETTERS
Volume 50, Issue 24, Pages 2914-2916Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.03.194
Keywords
Carbohydrates; Benzylidene acetals; Reductive ring opening; Regioselective
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Benzylidene-type cyclic acetals of carbohydrates undergo efficient reductive ring opening using BH3 center dot THF and a catalytic amount of TMSOTf at room temperature. 4,6-O-Benzylidene-hexopyranosides afford the corresponding 4-O-benzyl ethers exclusively, in high yields. Other benzylidene-type acetals, such as naphthylmethylene and 4-methoxybenzylidene acetals are also cleaved with the same reagent. The conversions are highly regio- and stereoselective and afford benzyl-type ethers in excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.
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