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

[11] 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

[12] USE OF THE ANOMERIC ALLYLATION REACTION IN NATURAL-PRODUCTS SYNTHESIS - A STEREOCONTROLLED SYNTHESIS OF METHYL DEOXYPSEUDOMONATE-B [J].

KOZIKOWSKI, AP ;

SORGI, KL .

TETRAHEDRON LETTERS, 1984, 25 (20) :2085-2088

[13] DEOXY-NITROSUGARS .17. SYNTHESIS OF KETOSE-DERIVED NUCLEOSIDES FROM 1-DEOXY-1-NITRORIBOSE [J].

MAHMOOD, K ;

VASELLA, A ;

BERNET, B .

HELVETICA CHIMICA ACTA, 1991, 74 (07) :1555-1584

[14]

Moffatt JG, 1979, NUCLEOSIDE ANALOGUES, P71

[15]

PAULMIER C, 1986, SELENIUM REAGENTS IN

[16]

ROBINS MJ, 1974, TETRAHEDRON LETT, P3369

[17] SYNTHESIS OF NEW 2',3'-MODIFIED URIDINE DERIVATIVES FROM 2',3'-ENE-2'-PHENYLSELENONYL URIDINE BY MICHAEL ADDITION-REACTIONS [J].

TONG, W ;

XI, Z ;

GIOELI, C ;

CHATTOPADHYAYA, J .

TETRAHEDRON, 1991, 47 (20-21) :3431-3450

[18] MICHAEL ADDITION-REACTIONS OF ALPHA,BETA-ENE-3'-PHENYLSELENONE OF URIDINE - NEW SYNTHESIS OF 2',3'-DIDEOXY-RIBO-AZIRIDINO-AMINO, 2',3'-DIDEOXY-2',3'-RIBO-CYCLOPROPYL-AMINO AND 2,2'-O-ANHYDRO-3'-DEOXY-3'-AMINO URIDINE DERIVATIVES [J].

WU, JC ;

CHATTOPADHYAYA, J .

TETRAHEDRON, 1989, 45 (14) :4507-4522

[19]

YOSHIMURA Y, 1991, TETRAHEDRON LETT, V35, P4549

← 1 2 →