The Journal of organic chemistry

Syntheses with Partially Benzylated Sugars. V. 1 Substitution at Carbon 4 in an Aldose. The Synthesis of 4-O-Methyl-β-D-arabinopyranose

HG Fletcher Jr, HW Diehl

Index: Fletcher,H.G.; Diehl,H.W. Journal of Organic Chemistry, 1965 , vol. 30, p. 2321 - 2323

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Citation Number: 10

Abstract

The readily accessible 2, 3, 5-tri-O-benzyl-~-arabinofuranose (I) was converted successively to 40-benzoyl-2, 3, 5-tri-O-benzyl-~-arabinose diethyl dithioacetal (111) and 40-benzoyl-2, 3, 5-tri-O-benzyl-~-arabinose dibenzyl acetal (VI). Replacement of the benzoyl group in the latter compound by methyl, followed by hydrogenolysis of the five benzyl groups, afforded crystalline 4-O-methyl-@-D-arabinopyranose (IX). This synthesis may be regarded as ...