174019-06-8Relevant articles and documents
Aminolysis and alkaline hydrolysis of protected 1-hydroxybenzotriazol-1-yl esters of adenosine 5'-phosphorothioate and -phosphorodithioate
Reese, Colin B.,Shek, Louise H. K.,Zhao, Zhengyun
, p. 3077 - 3084 (2007/10/03)
When 2',3'-bis-O-(methoxyacetyl)-6-N-(9-phenylxanthen-9-yl)adenosine 9, which was prepared from adenosine in six steps and in ca. 70percent overall yield, was treated with putative tri(benzotriazol-1-yl) phosphorothioate 11 and the products then worked up with aq. triethylamine, the triethylammonium salt of the protected benzotriazol-1-yl ester 6a of adenosine 5'-phosphorothioate was obtained in high yield.The corresponding adenosine 5'-phosphorodithioate derivative 6b was prepared, also in high yield, by a modification of the latter procedure involving work-up with hydrogen sulfide and triethylamine.Reaction between the phosphorothioate derivative 6a and methylamine or morpholine gave the phosphorothioamidates 12a and 13a, respectively, in high yields; in the same way, the phosphorodithioate derivative 6b was converted into the phosphorodithioamidates 12b and 13b.Treatment of the phosphorothioate derivative 6a first with aq. alkali and then with aq. acid gave a mixture of adenosine 5'-phosphorothioate 15a and adenosine 3',5'-cyclic phosphorothioate 17a.When the phosphorodithioate derivative 6b was treated in the same way, adenosine 3',5'-cyclic phosphorodithioate 17b was obtained in good yield.
