Thio-sugars. IV. Synthesis of carbohydrate 1,3-glycol (six-membered) thionocarbonates and their attempted O-S rearrangement.
Four six-membered cyclic thionocarbonates (two sec-sec and two prim-sec) were prepared and their radical-promoted O-S rearrangement reaction was examined. The results revealed that the reaction in six-membered rings is difficult compared with the simple rearrangement in five-membered rings. In the course of syntheses of the substrates, interesting acyl migration during the stannylation process occurred.
Tsuda
Y
Y
Faculty of Pharmaceutical Sciences, Kanazawa University, Japan.
Noguchi
S
S
Niino
H
H
D000215:Acylation; D002254:Carbonates / Q000737:chemistry*; D006018:Glycols / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
D002254:Carbonates; D006018:Glycols; D007202:Indicators and Reagents