URACIL AND ADENINE NUCLEOSIDES HAVING A 2',3'-BROMOVINYL STRUCTURE - HIGHLY VERSATILE SYNTHONS FOR THE SYNTHESIS OF 2'-C-BRANCHED AND 3'-C-BRANCHED 2',3'-UNSATURATED DERIVATIVES

被引：22

作者：

HARAGUCHI, K ^{[1
]}

ITOH, Y ^{[1
]}

TANAKA, H ^{[1
]}

AKITA, M ^{[1
]}

MIYASAKA, T ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1993年 / 49卷 / 07期

关键词：

BETA-HYDROXYSELENIDE; BROMOVINYL STRUCTURE; BRANCHED-SUGAR NUCLEOSIDE; ANTI-HIV AGENT; 2'; 3'-UNSATURATED NUCLEOSIDE;

D O I：

10.1016/S0040-4020(01)90190-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Preparation of 2'- and 3-bromo derivatives of 2',3'-unsaturated uracil and adenine nucleosides has been carried out starting from the corresponding beta-hydroxyselenides by way of bromination and successive selenoxide elimination. These compounds have been shown to serve as versatile synthons for the preparation of anti-HIV candidates, 2'-C- and 3'-C-branched 2',3'-unsaturated nucleosides, through palladium-catalyzed cross-coupling and halogen-lithium exchange reactions.

引用

页码：1371 / 1390

页数：20

共 50 条

[21] HOW DOES THE STERIC EFFECT DRIVE THE SUGAR CONFORMATION IN THE 3'-C-BRANCHED NUCLEOSIDES
PLAVEC, J
GARG, N
CHATTOPADHYAYA, J
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (12) : 1011 - 1014
[22] Preparation of 3′-C-branched uridine analogues, suitable for conversion into functionalism 3′-C-methylene derivatives
Winqvist, A
Strömberg, R
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2001, 20 (4-7): : 1389 - 1392
[23] A short, flexible route toward 2'-C-branched ribonucleosides
HarryOkuru, RE
Smith, JM
Wolfe, MS
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06): : 1754 - 1759
[24] 3'-C-BRANCHED 2'-DEOXY-5-METHYLURIDINES - SYNTHESIS, ENZYME-INHIBITION, AND ANTIVIRAL PROPERTIES
FEDOROV, II
KAZMINA, EM
NOVICOV, NA
GURSKAYA, GV
BOCHKAREV, AV
JASKO, MV
VICTOROVA, LS
KUKHANOVA, MK
BALZARINI, J
DECLERCQ, E
KRAYEVSKY, AA
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (24) : 4567 - 4575
[25] 2′-C-branched ribonucleosides.: 2.: Synthesis of 2′-C-β-trifluoromethyl pyrimidine ribonucleosides
Li, NS
Tang, XQ
Piccirilli, JA
ORGANIC LETTERS, 2001, 3 (07) : 1025 - 1028
[26] Synthesis of 3′-C- and 4′-C-branched oligodeoxynucleotides and the development of locked nucleic acid (LNA)
Wengel, J
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (04) : 301 - 310
[27] REACTION OF ORGANOMETALLIC REAGENTS WITH 2'-KETOURIDINE AND 3'-KETOURIDINE DERIVATIVES - SYNTHESIS OF URACIL NUCLEOSIDES BRANCHED AT THE 2'-POSITION AND 3'-POSITION
HAYAKAWA, H
TANAKA, H
ITOH, N
NAKAJIMA, M
MIYASAKA, T
YAMAGUCHI, K
IITAKA, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1987, 35 (06) : 2605 - 2608
[28] Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents (vol 54, pg 2209, 1998)
Hossain, N
van Halbeek, H
De Clercq, E
Herdewijn, P
TETRAHEDRON, 1998, 54 (21) : 5423 - 5423
[29] A simple and stereodivergent strategy for the synthesis of 3′-C-branched 2′,3′-dideoxynucleosides exploiting (Z)-but-2-en-1,4-diol and (R)-2,3-cyclohexylideneglyceraldehyde
Chattopadhyay, Angshuman
Goswami, Dibakar
Dhotare, Bhaskar
TETRAHEDRON LETTERS, 2006, 47 (27) : 4701 - 4705
[30] STEREOSPECIFIC SYNTHESIS AND MMR CONFORMATIONAL STUDIES OF GAMMA-BUTYROLACTONES OF NUCLEOSIDES AS CHIRAL SYNTHONS FOR THE PREPARATION OF 2'-C-BRANCHED-CHAIN AND 3'-C-BRANCHED-CHAIN NUCLEOSIDES
VELAZQUEZ, S
JIMENO, ML
HUSS, S
BALZARINI, J
CAMARASA, MJ
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25): : 7661 - 7670

← 1 2 3 4 5 →