NEW PROLINE DERIVED CHIRAL BUILDING-BLOCKS FOR NUCLEOSIDE METHYLPHOSPHONATE SYNTHESIS

被引：14

作者：

ROSMANITZ, P ^{[1
]}

EISENHARDT, S ^{[1
]}

BATS, JW ^{[1
]}

ENGELS, JW ^{[1
]}

机构：

[1] UNIV FRANKFURT,INST ORGAN CHEM,D-60439 FRANKFURT,GERMANY

来源：

TETRAHEDRON | 1994年 / 50卷 / 19期

关键词：

D O I：

10.1016/S0040-4020(01)85640-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

P-Prolyl-nucleoside-P-methyl-phosphanamidites P-chiral building blocks for nucleoside methylphosphonate synthesis were prepared by two different methods. First starting from dichloromethylphosphine 1 prochiral bis-proline-methylphosphines 3a-e were obtained. Their reaction with tritylthymidine in presence of an acid like tetrazole or better 2,6-di-tert. -butyl4-methylpyridinium-tetrafluoroborate furnished the amidites 5a-e. The absolute configuration of the phosphorus center could be determined by single crystal X-ray diffraction. Based on this determination configuration of the amidites 5a-e and 10a-e could be assigned by NMR spectroscopy. Alternatively starting from dichloromethylphosphine reaction with dimethoxytritylthymidine followed by addition of the proline derivative 2a-i in the presence of triethylamine yielded the Phosphorus-chiral amidites 10a-i with a de up to 81%.

引用

页码：5719 / 5734

页数：16

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