Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides.
The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc)(2) to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag(2)CO(3) and Cu(OAc)(2) (or DMSO) in acetonitrile. This arylation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides.
Li
Hou-Hua
HH
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, and School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No. 38, Beijing, 100191, China.
Ye
Xin-Shan
XS
D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D006219:Halogens / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D004987:Ethers; D006027:Glycosides; D006219:Halogens; D010165:Palladium; D007455:Iodine