Chloramine-T-mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions.
A metal-free, mild, efficient and chemoselective hydrolysis of several thioalkylglycosides (1) into their corresponding 1-hydroxy sugars (2) using sodium N-chloro-p-toluenesulfonamide trihydrate (chloramine-T) without affecting other functional groups is reported.
Medicinal Chemistry Division, Central Drug Research Institute, Lucknow 226-001, India. akmisra69@rediffmail.com
Anup Kumar
AK
Misra
Geetanjali
G
Agnihotri
D000080:Acetals / Q000737:chemistry*; D002700:Chloramines / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry*
D000080:Acetals; D002700:Chloramines; D016877:Oxidants; D013865:Thioglycosides; D014105:Tosyl Compounds; C016300:chloramine-T