120016-85-5Relevant academic research and scientific papers
A CONVENIENT ROUTE TO FUNCTIONALIZED BRANCHED-CHAIN SUGARS VIA A TOSYL-EPOXIDE DERIVATIVE
Ton-That, Thang
, p. 995 - 1006 (2007/10/02)
Starting from methyl 4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside-3-ulose 1 and proceeding through its corresponding tosyl-epoxide derivative 2, various branched-chain sugars (3-8) were prepared by nucleophilic and reductive ring openings.The presence of the sulfonylated oxirane group was found to be compatible with chemical transformations of the benzylidene acetal group (9-11), allowing facile access to the 6-deoxyhexoses (12-13).
A New Approach to the Stereospecific Synthesis of Branched-chain Sugars
Thang, Ton That,Laborde, Maria de los A.,Olesker, Alain,Lukacs, Gabor
, p. 1581 - 1582 (2007/10/02)
Darzens condensation of two readily available carbohydrate ketones with chloromethyl p-tolyl sulphone gave stereospecifically α,β-epoxy sulphones, in the presence of azide ion the latter afforded branched-chain functionalized azido-sugars.
