Stereoselective synthesis of α-glycosyl azides by ring-opening of 1,6-anhydrosugars with trimethylsilyl azide.
We describe here an expedient and highly stereoselective procedure for the synthesis of α-glycosyl azides. Treatment of 1,6-anhydrosugars with trimethylsilyl azide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl azides. All the reactions were highly stereoselective and afforded the α-glycosyl azides in good to excellent yields.
College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China.
Tianyu
T
Cui
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
Raymond
R
Smith
College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China; Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland. Electronic address: xiangming.zhu@ucd.ie.
Xiangming
X
Zhu
D001386:Azides / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D001386:Azides; D006027:Glycosides; D012821:Silanes; C438544:azidotrimethylsilane
1,6-Anhydrosugar; Glycosyl azide; Ring-opening; Stereoselectivity