Tetrahedron

New proline derived chiral building blocks for nucleoside methylphosphonate synthesis

P Rosmanitz, S Eisenhardt, JW Bats, JW Engels

Index: Rosmanitz, Pia; Eisenhardt, Stefan; Bats, Jan W.; Engels, Joachim W. Tetrahedron, 1994 , vol. 50, # 19 p. 5719 - 5734

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Citation Number: 12

Abstract

P-Prolyl-nucleoside-P-methyl-phosphonamidites, 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.- butyl-4-methyl-pyridinium-tetrafluoroborate furnished the amidites 5a-e. The absolute ...