SYNTHESIS OF S-ALKYL ESTERS OF PROTECTED 2'-DEOXYRIBONUCLEOSIDE 3'-PHOSPHOROTHIOATES - BUILDING-BLOCKS FOR THE LARGE-SCALE SYNTHESIS OF PHOSPHOROTHIOATE ANALOGS OF OLIGODEOXYRIBONUCLEOTIDES BY THE PHOSPHOTRIESTER APPROACH IN SOLUTION

被引：17

作者：

LIU, XH ^{[1
]}

REESE, CB ^{[1
]}

机构：

[1] UNIV LONDON KINGS COLL,DEPT CHEM,LONDON WC2R 2LS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 13期

关键词：

D O I：

10.1039/p19950001685

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triethylammonium salts of 5'-O-(9-phenylxanthen-9-yl)-2'-deoxyriboucleoside 3'-(H-phosphonates) 23, 33a, 33b and 33c, derived from thymidine, 6-N-pivaloyl-2'-deoxyadenosine, 4-N-benzoyl-2'-deoxycytidine and 2-N-phenylacetyl-2'-deoxyguanosine, react with N-(2-cyanoethylsulfanyl)phthalimide 21 in the presence of chlorotrimethylsilane and 4-methylmorpholine to give the corresponding 3'-phosphorothioate S-(2-cyanoethyl) esters 24c, 34a, 34b and 34c, respectively, in good yield. The S-(2-cyanoethyl) group appears to be suitable for the protection of internucleotide linkages in the synthesis of oligonucleotide phosphorothioates by the phosphotriester approach in solution.

引用

页码：1685 / 1694

页数：10

共 6 条

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[2] SYNTHESIS OF THE 3'-TERMINAL HALF OF YEAST ALANINE TRANSFER RIBONUCLEIC-ACID (TRANSFER RNAALA) BY THE PHOSPHOTRIESTER APPROACH IN SOLUTION .1. PREPARATION OF THE NUCLEOSIDE BUILDING-BLOCKS
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[3] DIASTEREOMERS OF NUCLEOSIDE 3'-O-(2-THIO-1,3,2-OXATHIA(SELENA)PHOSPHOLANES) - BUILDING-BLOCKS FOR STEREOCONTROLLED SYNTHESIS OF OLIGO(NUCLEOSIDE PHOSPHOROTHIOATE)S
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[4] Building-blocks for the solution phase synthesis of oligonucleotides:: Regioselective hydrolysis of 3′,5′-dilevulinyl-2′-deoxynucleosides using an enzymatic approach.
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U171 - U171
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BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2018, 91 (08) : 1258 - 1263
[6] EFFICIENT SYNTHESIS OF (1S,5S)-4-ALKYL-6,6-DIMETHYLBICYCLO[3.1.1]HEPT-3-EN-2-ONES FROM (1R,5S)-(+)-NOPINONE AND PREPARATION OF SOME CHIRAL BUILDING-BLOCKS SUITABLE FOR THE ASYMMETRIC-SYNTHESIS
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