Silver(I) oxide mediated selective monoprotection of diols in pyranosides.
The reaction of 4, 6-O-benzylidene-d-pyranosides with a stoichiometric amount of TsCl, AcCl, and BzCl in the presence of silver(I) oxide and a catalytic amount of potassium iodide led to monosubstituted derivatives in high regioselectivity and in good yields.
The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University, Xue Yuan Road #38, Beijing 100083, P. R. China.
Haisheng
H
Wang
Ji
J
She
Li-He
LH
Zhang
Xin-Shan
XS
Ye
D002384:Catalysis; D006027:Glycosides / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D011193:Potassium Iodide / Q000737:chemistry; D011714:Pyrans / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D006027:Glycosides; D007202:Indicators and Reagents; D010087:Oxides; D011714:Pyrans; D018030:Silver Compounds; D011193:Potassium Iodide; C040225:disilver oxide