二核苷（N3'→MeP5'）甲膦酰胺酯的合成

Synthesis of dinucleoside (N3'-->MeP5') methanephosphonamidates.

作者信息

Nawrot Barbara, Sobczak Milena, Antoszczyk Slawomir

机构信息

Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland.

出版信息

Org Lett. 2002 May 16;4(10):1799-802. doi: 10.1021/ol0259084.

DOI:10.1021/ol0259084

PMID:12000302

Abstract

[structure: see text] Three different approaches were used for the synthesis of dinucleoside methanephosphonamidates [3'-NH-P(O)(CH3)O-5'], starting from dichloromethylphosphine or dichloromethanephosphonate as the phosphorus-containing moiety. 5'-DMT-3'-amino-3'-deoxythymidine and N(4)-benzoyl-5'-DMT-3'-amino-2',3'-dideoxycytidine were used as the aminonucleoside precursors and the respective 3'-protected nucleosides (thymidine or N(4)-benzoyl-2'-deoxycytidine) as the 5'-hydroxyl reagents.

摘要

[结构：见正文] 以二氯甲基膦或二氯甲烷膦酸酯作为含磷部分，采用三种不同方法合成了二核苷甲膦酰胺酸酯[3'-NH-P(O)(CH3)O-5']。5'-二甲氧基三苯甲基-3'-氨基-3'-脱氧胸苷和N(4)-苯甲酰基-5'-二甲氧基三苯甲基-3'-氨基-2',3'-二脱氧胞苷用作氨基核苷前体，相应的3'-保护核苷（胸苷或N(4)-苯甲酰基-2'-脱氧胞苷）用作5'-羟基试剂。