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A novel synthesis of 5-thio-D-glucose

✍ Scribed by H. Driguez; B. Henrissat


Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
115 KB
Volume
22
Category
Article
ISSN
0040-4039

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Three routes were investigated for the conversion of D-glucose into the title compound. In the first approach, reduction of the 5,6-thiirane ring of 5,6-dideoxy-5,6-epithio-1,2-O-isopropylidene-t~-D-glucofuranose (17) as well as that of its 3-O-allyl derivative (13) with lithium aluminium hydride wa

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5-Thio-L-fucopyranose tetraacetate was synthesized in 11 steps from 5-O-trityl-D-arabinofuranose or D-arabinose diethyl dithioacetal by one-carbon elongation at C-5. Highly diastereoselective addition of MeLi in ether to a 1,2-O-isopropylidene-[J-D-arabino-pentodialdo-l,4-furanose derivative was ach