1-ALKYLTHIOALKYLATION OF NUCLEOSIDE HYDROXYL FUNCTIONS AND ITS SYNTHETIC APPLICATIONS - A NEW VERSATILE METHOD IN NUCLEOSIDE CHEMISTRY

被引：43

作者：

ZAVGORODNY, S

POLIANSKI, M

BESIDSKY, E

KRIUKOV, V

SANIN, A

POKROVSKAYA, M

GURSKAYA, G

LONNBERG, H

AZHAYEV, A

机构：

[1] UNIV TURKU,DEPT CHEM,SF-20500 TURKU 50,FINLAND

[2] RUSSIAN ACAD SCI,INST MOLEC BIOL,MOSCOW 117984,RUSSIA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 51期

关键词：

NUCLEOSIDE; ALKYLTHIOALKYLATION; SULFIDE; SULFOXIDE; SULFONE;

D O I：

10.1016/0040-4039(91)80543-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of appropriately protected nucleosides with a mixture of acetic acid, acetic anhydride and dialkylsulfoxide was shown to give O-(1-alkylthioalkylated) nucleosides that were oxidized to the corresponding sulfoxides and sulfones, or converted via O-halogenomethyl derivatives to various O-substituted nucleosides.

引用

页码：7593 / 7596

页数：4

共 17 条

[1]

BOCHKAREV AV, UNPUB BIOORG KHIM

[2]

CHOWDHURY PK, 1983, TETRAHEDRON LETT, V24, P4485

[3] PROTECTION OF HYDROXYL GROUP WITH VINYL THIOETHERS [J].

COHEN, LA ;

STEELE, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2333-&

[4]

COREY EJ, 1975, TETRAHEDRON LETT, P3269

[5]

GAVAGNIN M, 1989, NUCLEOS NUCLEOT, V8, P1315

[6]

HANESSIA.S, 1970, CHEM IND-LONDON, P1436

[7]

HANNSKE F, 1984, TETRAHEDRON, V40, P125

[8] SYNTHESIS AND ANTI-HIV ACTIVITY OF DIFFERENT SUGAR-MODIFIED PYRIMIDINE AND PURINE NUCLEOSIDES [J].

HERDEWIJN, P ;

BALZARINI, J ;

BABA, M ;

PAUWELS, R ;

VANAERSCHOT, A ;

JANSSEN, G ;

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) :2040-2048

[9] VOM ADENOSIN ABGELEITETE THIOATHER UND S-OXIDE [J].

KUHN, R ;

JAHN, W .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (06) :1699-&

[10] PERIODATE OXIDATION OF SULFIDES TO SULFOXIDES - SCOPE OF REACTION [J].

LEONARD, NJ ;

JOHNSON, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) :282-&

← 1 2 →