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.
Wang
Haisheng
H
The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University, Xue Yuan Road #38, Beijing 100083, P. R. China.
She
Ji
J
Zhang
Li-He
LH
Ye
Xin-Shan
XS
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