Chemoselective per-O-trimethylsilylation and homogeneous N-functionalisation of amino sugars.
A highly efficient CH3CN-promoted hexamethyldisilazane per-O-trimethylsilylation of amino sugars was developed. Its applications in homogenous N-functionalisation and a concise synthesis of glucosamine 6-phosphate are described.
Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan. wangcc@chem.sinica.edu.tw.
A Abragam
AA
Joseph
Vijay M
VM
Dhurandhare
Chun-Wei
CW
Chang
Ved Prakash
VP
Verma
Girija Prasad
GP
Mishra
Chiao-Chu
CC
Ku
Chun-Cheng
CC
Lin
Cheng-Chung
CC
Wang
D000097:Acetonitriles / Q000737:chemistry; D000606:Amino Sugars / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D019298:Glucose-6-Phosphate / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry
D000097:Acetonitriles; D000606:Amino Sugars; D017646:Organosilicon Compounds; D011725:Pyridines; C001293:glucosamine 6-phosphate; D019298:Glucose-6-Phosphate; C024548:hexamethylsilazane; D005944:Glucosamine; D009584:Nitrogen; C023666:pyridine; D010100:Oxygen