A direct and stereospecific approach to the synthesis of alpha-glycosyl thiols.
A new simple method for the synthesis of alpha-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded alpha-glycosyl thiols in very high yields and in a stereospecific way.
Dere
Ravindra T
RT
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
Wang
Yingxi
Y
Zhu
Xiangming
X
D002384:Catalysis; D008698:Mesylates / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D008698:Mesylates; D013438:Sulfhydryl Compounds; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate