An efficient and selective method for preparing glycosyl sulfoxides by oxidizing glycosyl sulfides with OXONE or t-BuOOH on SiO2.
Silica gel adsorbed with OXONE or t-BuOOH was used as a mild oxidant to selectively oxidize glycosyl sulfides to corresponding sulfoxides in good yields and without sulfones formation. This method was also found compatible with various other functional groups in the glycosides.
Chen
Ming-Yi
MY
Institute of Chemistry, Academia Sinica, 128, Sec. 2, Yen-Chiu-Yuan Rd. Nankang, 115, Taipei, Taiwan, ROC.
Patkar
Laxmikant Narhari
LN
Chen
Hui-Ting
HT
Lin
Chun-Cheng
CC
D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D010084:Oxidation-Reduction; D012822:Silicon Dioxide / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry; D013464:Sulfuric Acids / Q000737:chemistry*; D013997:Time Factors; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
D006027:Glycosides; D013440:Sulfides; D013454:Sulfoxides; D013464:Sulfuric Acids; D012822:Silicon Dioxide; D020122:tert-Butylhydroperoxide; C048813:potassium peroxymonosulfuric acid