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ChemInform Abstract: A Highly Stereoselective β-(1→4)-Glycosidic Bond Formation by Reductive Cleavage of Cyclic Orthoesters.

✍ Scribed by T. IIMORI; H. OHTAKE; S. IKEGAMI

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

A Highly Stereoselective β-(1→4)-Glycosidic Bond Formation by Reductive Cleavage of Cyclic Orthoesters.

-Reduction of the orthoester (I) under the conditions shown provides the desired glycoside (II) with high β-selectivity. Application of a LiAlH4/AlCl3 reagent to the glycosidic spiro-orthoesters (III) results in formation of sterically congested glycosyl-β-(1→ 4)-glycosides. The latter transformation is especially valuable for the synthesis of glycoside (IV) which is one of the most difficult tasks in carbohydrate chemistry. -(IIMORI, T.;

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