A general and chemoselective synthesis of phosphoramidates through reaction of silylated nucleoside di- and triphosphates with silylated amines containing multifunctional groups.
An approach to various phosphoramidates has been developed through one-pot chemoselective reaction of nucleoside di- and triphosphates with 3'-amino-3'-deoxythymidine, d-glucosamine, and peptides mediated by trimethylsilyl chloride, and the corresponding conjugates via the linkage of phosphate were obtained. The method could be generally applied for the synthesis of phosphoramidates without any preprotection of polyphosphates and amines containing multifunctional groups.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, PR China.
Jigang
J
Zhu
Hua
H
Fu
Yuyang
Y
Jiang
Yufen
Y
Zhao
D000577:Amides / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry*; D015224:Dideoxynucleosides / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry; D009711:Nucleotides / Q000138:chemical synthesis*; D010455:Peptides / Q000737:chemistry; D010756:Phosphoric Acids / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D000577:Amides; D000588:Amines; D015224:Dideoxynucleosides; D009711:Nucleotides; D010455:Peptides; D010756:Phosphoric Acids; D012821:Silanes; D014297:Trimethylsilyl Compounds; C019252:3'-aminothymidine; C011067:phosphoramidic acid; D005944:Glucosamine