K. Polchow, J. Voss
Feb 1, 2005
Citations
0
Influential Citations
4
Citations
Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
Abstract 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 thietanosugar methyl 4,6-anhydro-1,3-di-O-mesyl-4-thio-α -D-tagatofuranoside. Methyl β -D-fructofuranoside gave the corresponding 6-S-thioacetate and, with excess thioacetic acid, the 1-S, 6-S-bis-thioacetate. Whereas this mono-thioacetate did not yield a thietano derivative, the bis-thioacetate gave the bis-thietane methyl 1,3:4,6-dianhydro-1,4-dithio-β -D-sorbofuranoside with sodium hydrogen carbonate.