A facile preparation of uronates via selective oxidation with TEMPO/KBr/Ca(OCl)(2) under aqueous conditions.
Addition of solid Ca(OCl)(2) as the terminal oxidant in the TEMPO-mediated selective oxidation has the benefit of easier operation. A variety of partially protected saccharide derivatives (1a-l) have been successfully converted into the corresponding uronate derivatives, including disaccharide building blocks for GAG fragments and precursors to saponins. The beneficial effect of Aliquat 336 was also disclosed in the oxidation of certain substrates.
Lin
Feng
F
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
Peng
Wenjie
W
Xu
Wen
W
Han
Xiuwen
X
Yu
Biao
B
D001965:Bromides / Q000737:chemistry*; D017610:Calcium Compounds / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002845:Chromatography; D003497:Cyclic N-Oxides / Q000737:chemistry*; D008956:Models, Chemical; D008969:Molecular Sequence Data; D010100:Oxygen / Q000737:chemistry; D017680:Potassium Compounds / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry; D012973:Sodium Hypochlorite / Q000737:chemistry; D013997:Time Factors; D014574:Uronic Acids / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D001965:Bromides; D017610:Calcium Compounds; D003497:Cyclic N-Oxides; D017680:Potassium Compounds; D012503:Saponins; D014574:Uronic Acids; D014867:Water; C004488:calcium hypochlorite; D012973:Sodium Hypochlorite; C039004:potassium bromide; D010100:Oxygen; C003959:TEMPO