ANOMERIC MANIPULATION OF NUCLEOSIDES - STEREOSPECIFIC ENTRY TO 1'-C-BRANCHED URACIL NUCLEOSIDES

被引：20

作者：

HARAGUCHI, K ^{[1
]}

ITOH, Y ^{[1
]}

TANAKA, H ^{[1
]}

YAMAGUCHI, K ^{[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 | 1993年 / 34卷 / 43期

关键词：

1'; 2'-UNSATURATED NUCLEOSIDE; 1'-C-BRANCHED URACIL NUCLEOSIDE; ELECTROPHILIC ADDITION; ORGANOSILICON REAGENT; C-C BOND FORMATION;

D O I：

10.1016/S0040-4039(00)91829-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Uracil nucleosides variously branched at die anomeric position have been synthesized through stereoselective bromo-pivaloyloxylation of a 1',2'-unsaturated derivative and successive SnCl4-promoted nucleophilic substitution with organosilicon reagents. This constitutes the first example of C-C bond formation at the anomeric position of nucleoside.

引用

页码：6913 / 6916

页数：4

共 19 条

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TETRAHEDRON, 1993, 49 (07) :1371-1390

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

HARAGUCHI, K ;

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

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

HARAGUCHI, K ;

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

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

HARAGUCHI, K ;

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ITOH, Y ;

MIYASAKA, T .

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

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

HARAGUCHI, K ;

TANAKA, H ;

ITOH, Y ;

SAITO, S ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1992, 33 (20) :2841-2844

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