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Australian Journal of Chemistry Australian Journal of Chemistry Society
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RESEARCH ARTICLE

A New Approach to Some 1,6-Dideoxy 1,6-Epithio Sugars

H Driguez, JC Mcauliffe, RV Stick, DMG Tilbrook and SJ Williams

Australian Journal of Chemistry 49(3) 343 - 348
Published: 1996

Abstract

The treatment of hexopyranosyl bromides, also activated at C6 (Br, OTs, OMs), with H2S/HCONMe2 under basic conditions gives rise to 1,6-dideoxy 1,6-epithio sugars. One such sugar has been further transformed into the synthetically useful 3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactose. The treatment of this epoxide with sodium azide and with cyclohexylamine is described. An analogous treatment of one doubly activated hexopyranosyl bromide with sodium hydrogen selenide has led to a novel 1,6-dideoxy 1,6-episeleno sugar which displayed interesting n.m.r. spectra. Finally, in an attempt to prepare 1,6-dideoxy 1,6-epidithio sugars, a tetraalkylammonium tetrathiomolybdate reagent was found to be the reagent of choice for converting doubly activated hexopyranosyl bromides into 1,6-dideoxy 1,6-epithio sugars.

https://doi.org/10.1071/CH9960343

© CSIRO 1996

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