Chemical and Stereochemical Aspects of Oxidative Coupling of HPhosphonate and H-Phosphonothioate Diesters. Reactions with N,N-, N,Oand O,O-Binucleophiles

Title: Chemical and Stereochemical Aspects of Oxidative Coupling of HPhosphonate and H-Phosphonothioate Diesters. Reactions with N,N-, N,Oand O,O-Binucleophiles

Volume: 2 Issue: 2

Author(s): Johan Nilsson, Adam Kraszewski and Jacek Stawinski

Affiliation:

Keywords: h-phosphonates, h-phosphonothioates, binucleophiles, oxidative coupling

Abstract: Efficient protocols for oxidative coupling of dinucleoside H-phosphonate and dinucleoside Hphosphonothioate diesters with 6-aminohexan-1-ol, hexane-1,6-diamine, and hexane-1,6-diol, promoted by iodine were developed. In the instance of coupling with O-nucleophiles, the presence of t-butyldiphenylsilyl chloride and excess of iodine during oxidative coupling were found to have beneficial effect for these reactions in terms of rates and purity of the formed products.

Cite this article as:

Nilsson Johan, Kraszewski Adam and Stawinski Jacek, Chemical and Stereochemical Aspects of Oxidative Coupling of HPhosphonate and H-Phosphonothioate Diesters. Reactions with N,N-, N,Oand O,O-Binucleophiles, Letters in Organic Chemistry 2005; 2 (2) . https://dx.doi.org/10.2174/1570178053202937