Preparation of anhydro-thiohexofuranosides from methyl fructofuranosides via the thio-Mitsunobu reaction
Methyl α-D-fructofuranoside was transformed regioselectively into the corresponding 6-S-thioacetate in one step by use of the thio-Mitsunobu reaction. Reaction of the trimesylate derived from this thioacetate with sodium hydrogen carbonate led to the thie
Polchow, Kerstin,Voss, Juergen
p. 1755 - 1768
(2007/10/03)
Acetalation studies. Part IX. Reaction of sucrose and some related sugars with acetone in the presence of iodine; a novel cleavage-isopropylidenation method
An efficient cleavage-isopropylidenation reaction of sucrose, catalyzed by iodine, is described.Related D-fructofuranosyl-containing oligosaccharides and their individual monosaccharide units were treated in a similar manner to yield isopropylidenated monosaccharide derivatives.The reaction conditions are particularly mild and selective.Some mechanistic aspects of the procedure are also discussed.
Verhart, Cor G. J.,Caris, Brigitte M. G.,Zwanenburg, Binne,Chittenden, Gordon J. F.
p. 348 - 352
(2007/10/02)
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