The case for configurational stability of H-phosphonate diesters in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU).

Abstract:

:Configurational stability of dinucleoside H-phosphonates and the stereochemical course of their sulfurisation in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU) were investigated using 31P NMR spectroscopy. It was found that under the reaction conditions and irrespective of the type of protecting groups present in the nucleoside moieties, the H-phosphonate diesters investigated did not undergo any detectable epimerisation at the phosphorus centre, and their sulfurisation with elemental sulfur in the presence of DBU, proceeded stereospecifically. Thus, we could not confirm reports from another laboratory on a stereoselective course of sulfurisation of H-phosphonate diesters and the corresponding acylphosphonates in the presence of DBU.

journal_name

Bioorg Med Chem

authors

Johansson T,Stawinski J

doi

10.1016/s0968-0896(01)00140-7

subject

Has Abstract

pub_date

2001-09-01 00:00:00

pages

2315-22

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(01)00140-7

journal_volume

9

pub_type

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