title: Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars.
abstract: Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl thiols. All the reactions were highly stereoselective and afforded the α-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding α-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to α-glycosyl thiols of great value was established.
authors: 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: Xiangming
authors: X
authors: Zhu
authors: Ravindra T
authors: RT
authors: Dere
authors: Junyan
authors: J
authors: Jiang
authors: Lei
authors: L
authors: Zhang
authors: Xiaoxia
authors: X
authors: Wang
mesh_terms: D032701:Biomimetics / Q000379:methods*; D002236:Carbohydrate Conformation; D060326:Chemistry Techniques, Synthetic; D006027:Glycosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
chemical_list: D006027:Glycosides; D009844:Oligosaccharides; D013438:Sulfhydryl Compounds; D014297:Trimethylsilyl Compounds