STEREOSELECTIVE SYNTHESIS OF 4'-C-BRANCHED 2',3'-DIDEHYDRO-2',3'-DIDEOXY NUCLEOSIDES BASED ON SNCL4-PROMOTED ALLYLIC REARRANGEMENT

被引：20

作者：

HARAGUCHI, K ^{[1
]}

TANAKA, H ^{[1
]}

ITOH, Y ^{[1
]}

SAITO, S ^{[1
]}

MIYASAKA, T ^{[1
]}

机构：

[1] SHOWA UNIV,SCH PHARMACEUT SCI,HATANODAI 1-5-8,SHINAGAWA KU,TOKYO 142,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 20期

关键词：

3'; 4'-UNSATURATED URACIL NUCLEOSIDE; ALLYLIC REARRANGEMENT; ORGANOSILICON REAGENT; 2'; 3'-DIDEHYDRO-2'; 3'-DIDEOXYURIDINE; 4'-C-BRANCHED NUCLEOSIDE;

D O I：

10.1016/S0040-4039(00)78874-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on SnCl4-promoted allylic rearrangement between a 3',4'-unsaturated uracil nucleoside and organosilicon reagents, stereoselective introduction of carbon functionalities to the 4'-position has been accomplished, disclosing a new entry for a series of 4'-C-branched nucleosides of biological interests.

引用

页码：2841 / 2844

页数：4

共 16 条

[1] TITANIUM TETRACHLORIDE PROMOTED REACTIONS OF ALLYLIC TRIMETHYLSILANES AND OXETANE [J].

CARR, SA ;

WEBER, WP .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) :2782-2785

[2]

DECLERCQ E, 1991, J ACQ IMMUN DEF SYND, V4, P207

[3] PREPARATION AND REACTIONS OF 2'-VINYL AND 3'-VINYL BROMIDES OF URACIL NUCLEOSIDES - VERSATILE SYNTHONS FOR ANTI-HIV AGENTS [J].

HARAGUCHI, K ;

ITOH, Y ;

TANAKA, H ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1991, 32 (28) :3391-3394

[4] SELENOXIDE ELIMINATION FOR THE SYNTHESIS OF UNSATURATED-SUGAR URACIL NUCLEOSIDES [J].

HARAGUCHI, K ;

TANAKA, H ;

MAEDA, H ;

ITOH, Y ;

SAITO, S ;

MIYASAKA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5401-5408

[5] NUCLEOSIDIC ENOL ESTERS - A VERSATILE TOOL FOR THE SYNTHESIS OF 3'-CARBON-SUBSTITUTED NUCLEOSIDES [J].

HARAGUCHI, K ;

TANAKA, H ;

ITOH, Y ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1991, 32 (06) :777-780

[6] ADDITION OF CARBON RADICALS TO 4',5'-UNSATURATED URACILNUCLEOSIDES BY THE USE OF ORGANOSELENIUM REAGENTS - A NEW STEREOSELECTIVE ENTRY TO C-C BOND FORMATION AT THE 5'-POSITION [J].

HARAGUCHI, K ;

TANAKA, H ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1990, 31 (02) :227-230

[7] NUCLEOPHILIC AND ORGANOMETALLIC DISPLACEMENT-REACTIONS OF ALLYLIC COMPOUNDS - STEREOCHEMISTRY AND REGIOCHEMISTRY [J].

MAGID, RM .

TETRAHEDRON, 1980, 36 (13) :1901-1930

[8]

Moffatt JG, 1979, NUCLEOSIDE ANALOGUES, P71

[9] SYNTHESIS OF 4'-CYANOTHYMIDINE AND ANALOGS AS POTENT INHIBITORS OF HIV [J].

OYANG, C ;

WU, HY ;

FRASERSMITH, EB ;

WALKER, KAM .

TETRAHEDRON LETTERS, 1992, 33 (01) :37-40

[10] 4'-SUBSTITUTED NUCLEOSIDES AS INHIBITORS OF HIV - AN UNUSUAL OXETANE DERIVATIVE [J].

OYANG, C ;

KURZ, W ;

EUGUI, EM ;

MCROBERTS, MJ ;

VERHEYDEN, JPH ;

KURZ, LJ ;

WALKER, KAM .

TETRAHEDRON LETTERS, 1992, 33 (01) :41-44

← 1 2 →