title: Efficient synthesis of methylene exo-glycals: another use of glycosylthiomethyl chlorides.
abstract: 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.
authors.affiliation: Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland. xiangming.zhu@ucd.ie
authors.forename: Xiangming
authors.initials: X
authors.lastname: Zhu
authors.forename: Ying
authors.initials: Y
authors.lastname: Jin
authors.forename: John
authors.initials: J
authors.lastname: Wickham
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry
chemical_list: D006027:Glycosides; C483915:glycosylthiomethyl chloride; D013455:Sulfur