Efficient synthesis of methylene exo-glycals: another use of glycosylthiomethyl chlorides.
A new approach to the synthesis of methylene exo-glycals is described. Oxidation of glycosylthiolmethyl chloride (GTM-Cl) with mCPBA afforded the corresponding glycosylchloromethyl sulfone in almost quantitative yield, which underwent KOtBu-induced Ramberg-Bäcklund rearrangement to furnish the desired methylene exo-glycal in excellent yield.
Zhu
Xiangming
X
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland. xiangming.zhu@ucd.ie
Jin
Ying
Y
Wickham
John
J
D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry
D006027:Glycosides; C483915:glycosylthiomethyl chloride; D013455:Sulfur