Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Aminosugars. XXVIII. A Facile Synthesis of Benzyl α- and β-Kasugaminides via the Corresponding Abequosides
Juji YoshimuraKen-ichi SatoHironobu HashimotoKuniaki Shimizu
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1977 Volume 50 Issue 12 Pages 3305-3309

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Abstract

Synthesis of benzyl α- and β-kasugaminides (benzyl 2,4-diamino-2,3,4,6-tetradeoxy-α- and β-D-arabino-hexopyranosides) was carried out by the simultaneous substitution at 2,4-positions of 2,4-di-O-mesyl-abequosides (3,6-dideoxy-2,4-di-O-mesyl-α- and β-D-xylo-hexopyranosides) with sodium azide followed by hydrogenation. The substitution in N,N-dimethylformamide at higher temperature gave the elimination products (4-azido-2,3-unsaturated derivatives) and the subsequently rearranged products (3,4-unsaturated 2-azido derivatives), but, that in hexamethylphosphoric triamide at lower temperature gave the desired compounds in fairly good yields.

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