Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst.
Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.
Yan
Ming-Chung
MC
Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan.
Chen
Yeng-Nan
YN
Wu
Huan-Ting
HT
Lin
Chang-Ching
CC
Chen
Chien-Tien
CT
Lin
Chun-Cheng
CC
D000143:Acids / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D001597:Benzylidene Compounds / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D014638:Vanadates / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000143:Acids; D000475:Alkenes; D001597:Benzylidene Compounds; D002241:Carbohydrates; D008698:Mesylates; C510339:vanadyl triflate; D014867:Water; D014638:Vanadates; C013658:propylene