Diastereomers of thymidine 3'-O-(methanephosphonothioate): synthesis, absolute configuration and reaction with 3'-methoxyacetylthymidine under conditions of triester approach to oligonucleotide synthesis

• Published in: Acta biochimica polonica Vol. 34; no. 2; pp. 217 - 231
• Main Authors: Niewiarowski, W, Leśnikowski, Z J, Wilk, A, Guga, P, Okruszek, A, Uznański, B, Stec, W
• Format: Journal Article
• Language: English
• Published: Poland 1987
• Subjects: Organothiophosphorus Compounds - chemical synthesis; Stereoisomerism; Thymidine - analogs & derivatives; Thymidine - chemical synthesis
• ISSN: 0001-527X

Diastereomers of the title compound were obtained and absolute configuration was assigned by means of stereochemical correlation. Their reaction with 3'-O-methoxyacetylthymidine in the presence of triisopropylbenzenesulphonyl (4-nitro) triazole is neither chemo- nor stereo-selective and leads to diastereomeric pairs of dithymidyl (3',5')methanephosphonate and -methanephosphonothioate. Obtained results are discussed in terms of mechanism of activation of phosphodiesters under conditions known as "phosphotriester approach to oligonucleotide synthesis".