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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 118, 1996 - Issue 1
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Original Articles

31P-13C, 31P-1H SPIN-SPIN COUPLING AND STRUCTURAL ASSIGNMENT AND CONFORMATIONAL ANALYSIS OF EPIMERIC THYMIDINE-3′-YL BENZOIN PHOSPHATES

Yu-Ping Feng Bioorganic Phosphorus Chemistry Laboratory, Department of Chemistry, Tsinghua University, Beijing, 100084, P. R. China
,
Xin Chen Bioorganic Phosphorus Chemistry Laboratory, Department of Chemistry, Tsinghua University, Beijing, 100084, P. R. China
,
Nan-Ding Zhang Bioorganic Phosphorus Chemistry Laboratory, Department of Chemistry, Tsinghua University, Beijing, 100084, P. R. China
&
Yu-Fen Zhao Bioorganic Phosphorus Chemistry Laboratory, Department of Chemistry, Tsinghua University, Beijing, 100084, P. R. China
Pages 219-225 | Received 23 May 1996, Accepted 21 Aug 1996, Published online: 24 Sep 2006
 
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Abstract

A pair of epimeric thymidine-3′-yl benzoin phosphates 3 were produced from the ester exchange reaction of oxyphosphorane 1 with thymidine 2. Their structures were identified by using the 1H, 13C and 31P NMR spectra. The chemical bonds between the ribose 3′-C and a-C atoms to the phosphoryl group were confirmed by 31P-′13C and 31P-1H spin-spin coupling. The stereosensitive three-bond coupling constants 3JP-c and 3JP-H in each diastereomer of 3 have been measured, and used for an estimation of trans and gauche conformational analysis. The relative estimated dihedral angle of P-O-C-H was discussed.

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