Monatshefte fur Chemie p. 521 - 530 (2002)
Update date:2022-08-11
Topics:
Witczak, Zbigniew J.
Kaplon, Peter
Kolodziej, Mark
A new stereoselective synthesis of (1→3)-3-S-thiodisaccharides is described. Levoglucosenone-derived chiral building blocks produced by the selenium-mediated iodination at C-3 afforded 3-iodoketones in moderate yield. Iodine displacement with sulfur nucleophiles (1-thiols) resulted in 3-thiodisaccharides. Following reduction of the C-2 keto function constituted a new two-step general approach to these biologically important thiosugars.
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