247223-72-9Relevant academic research and scientific papers
A practical synthesis of 3'-thioguanosine and of its 3'- phosphoramidothioite (a thiophosphoramidite)
Matulic-Adamic, Jasenka,Beigelman, Leonid
, p. 2141 - 2150 (2007/10/03)
Starting from guanosine, an efficient method for the synthesis of 3'- thioguanosine (see 13) and of its 3'-phosphoramidothioite (see 23), suitable for automated incorporation into oligonucleotides, was developed. Reaction of 5'-N2-protected guanosine with 2-acetoxyisobutyryl bromide afforded stereoselectively the 2'-O-acetyl-3'-bromo-β-D-xylofuranosyl derivative 3, which was converted to a 7:3 mixture of the S-acyl ribofuranosyl intermediates 5 or 6 and the 3',4'-unsaturated by-product 4. The S-acylated nucleosides 5 and 6 were then converted in three steps to 5'-O-(4,4'- dimethoxytrityl)-3'-S-(pyridin-2-ylthio)-3'-thioguanosine (11), which served as a common intermediate for the preparation of free 3'-thionucleoside 13 and 3'-thionucleoside 3'-phosphoramidothioite 23.
