Synthesis, structure and reactivity of 5-pyranosyl-1, 3, 4-oxathiazol-2-ones

KG McMillan, MN Tackett, A Dawson, E Fordyce…

Index: McMillan, Keith G.; Tackett, Miles N.; Dawson, Alice; Fordyce, Euan; Paton, R. Michael Carbohydrate Research, 2006 , vol. 341, # 1 p. 41 - 48

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Citation Number: 18

Abstract

5-(1, 2, 3, 4-Tetra-O-acetyl-α-d-xylopyranos-5S-C-yl)-1, 3, 4-oxathiazol-2-one (8) has been prepared from glucuronamide in two steps and 73% overall yield by conversion to the tetra- O-acetyl derivative 7 followed by reaction with chlorocarbonylsulfenyl chloride. 5-(2, 3, 4-Tri- O-acetyl-β-d-xylopyranosyl)-1, 3, 4-oxathiazol-2-one (12) was synthesised from d-xylose by a four-step sequence involving conversion to the xylopyranosylnitromethane derivative 9, ...