Diastereomers of thymidine 3'-O-(methanephosphonothioate): synthesis, absolute configuration and reaction with 3'-methoxyacetylthymidine under conditions of triester approach to oligonucleotide synthesis.
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".
Niewiarowski
W
W
Department of Bioorganic Chemistry, Polish Academy of Sciences, Lódź.
Leśnikowski
Z J
ZJ
Wilk
A
A
Guga
P
P
Okruszek
A
A
Uznański
B
B
Stec
W
W
D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D009946:Organothiophosphorus Compounds; C054095:thymidine 3'-O-(methanephosphonothioate); C054096:3-O-methoxyacetylthymidine; D013936:Thymidine