Aminolysis and alkaline hydrolysis of protected 1-hydroxybenzotriazol-1-yl esters of adenosine 5'-phosphorothioate and -phosphorodithioate

被引:11
作者
Reese, CB
Shek, LHK
Zhao, ZY
机构
[1] Department of Chemistry, King's College London, London WC2R 2LS, Strand
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 24期
关键词
D O I
10.1039/p19950003077
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
When 2',3'-bis-O-(methoxyacetyl)-6-N-(9-phenylxanthen-9-yl)adenosine 9, which was prepared from adenosine in six steps and in similar to 70% 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.
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页码:3077 / 3084
页数:8
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