Pre-activation protocol leading to highly stereoselectivity-controllable glycosylations of oxazolidinone protected glucosamines.
Under pre-activation glycosylation conditions, the 4,6-di-O-acetyl-N-acetyloxazolidinone protected donor afforded either excellent beta- or alpha-stereoselectivity simply by means of the addition of hindered base TTBP or the absence of base, leading to the controllable stereochemistry of coupling reactions.
Geng
Yiqun
Y
The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd #38, Beijing, 100083, China.
Zhang
Li-He
LH
Ye
Xin-Shan
XS
D002236:Carbohydrate Conformation; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C527937:4,6-di-O-acetyl-N-acetyloxazolidinone; D023303:Oxazolidinones; D005944:Glucosamine