SYNTHESIS OF 2′-DEOXY-4′-C-HYDROXYMETHYL-4′-THIORIBONUCLEOSIDES AND THEIR 2′,3′-DIDEOXY AND 2′,3′-DIDEHYDRO-2′,3′-DIDEOXY ANALOGUES

被引：0

作者：

Nokami, Junzo ^{[1
]}

Mae, Masayuki ^{[1
]}

Fukutake, Satoshi ^{[1
]}

Ubuka, Tomoyuki ^{[1
]}

Yamada, Mitsuhiro ^{[1
]}

机构：

[1] Okayama Univ Sci, Fac Engn, Dept Appl Chem, Okayama 7000005, Japan

来源：

HETEROCYCLES | 2008年 / 76卷 / 02期

关键词：

4 '-Thioribonucleoside; Electrolysis; N-Glycosylation; Aldol Reaction; Pummerer Rearrangement;

D O I：

10.3987/COM-08-S(N)100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-2'-Deoxy-4'-C-hydroxymethyl-4'-thioribonucleosides (1) and their 2',3'-dideoxy- (2) and 2',3'-didehydro-2,3'-dideoxy- (3) analogues have been prepared from hydrothiophene derivatives 2,2-bis(benzyloxymethyl)-3-benzyloxytetrahydrothiophene (4), 2,2-bis(acetoxymethyl)tetrahydrothiophene (5) and 2,2-bis(acetoxymethyl)-2,5dihydrothiophene (6), respectively. Preparation of the compound 1 has been carried out via N-glycosylation of the corresponding sulfoxide 9, derived from 4 by m-CPBA oxidation, with trimethylsilylated pyrimidines and trimethylsilyl triflate (Kita-O'Niel-Matsuda's method; modified Pummerer rearrangement). On the other hand, the compounds 2 and 3 have been obtained via N-glycosylation of the corresponding 4'-thiofuranoses 7 and 8 with trimethylsilylated pyrimidines and SnCl4, respectively, while the compounds 7 and 8 have been prepared from compounds 5 and 6 by an electrochemical 2-acetoxylation, respectively.

引用

页码：1337 / 1360

页数：24

共 50 条

[31] NUCLEOSIDES AND NUCLEOTIDES .87. SYNTHESIS OF 2',3'-DIDEOXY-3'-METHYLIDENETHYMIDINE AND 2',3'-DIDEHYDRO-2',3'-DIDEOXY-3'-METHYLTHYMIDINE - DEOXYGENATION OF THE ALLYLIC ALCOHOL SYSTEM IN 3'-DEOXY-3'-METHYLIDENE-5-METHYLURIDINE
MATSUDA, A
OKAJIMA, H
UEDA, T
HETEROCYCLES, 1989, 29 (01) : 25 - 28
[32] Synthesis of 2′,3′-dideoxy-3′,3′-difluoro and 2′,3′-dideoxy-2′,2′-difluoropyranosyl nucleosides analogues of gemcitabine
Fernández, R
Castillón, S
TETRAHEDRON, 1999, 55 (28) : 8497 - 8508
[33] Synthesis and anti-HIV activity of D- and L-2′,3′-didehydro-2′,3′-dideoxy-2′-fluoro-4′-thiocytidines
Chu, CK
Choi, YS
Choo, H
Chong, YH
Lee, S
Zhu, W
Schinazi, RF
ANTIVIRAL RESEARCH, 2002, 53 (03) : A36 - A36
[34] NOVEL SYNTHESIS OF (+/-)-CIS-4-AMINO-2-CYCLOPENTENE-1-METHANOL, A KEY INTERMEDIATE IN THE PREPARATION OF CARBOCYCLIC 2',3'-DIDEHYDRO-2',3'-DIDEOXY NUCLEOSIDES
NORMAN, MH
ALMOND, MR
REITTER, BE
RAHIM, SG
SYNTHETIC COMMUNICATIONS, 1992, 22 (22) : 3197 - 3204
[35] Synthesis of carba analogues of 2′-deoxy-4′-C-(hydroxymethyl)nucleosides
Hrebabecky, H
CHEMISTRY OF NUCLEIC ACID COMPONENTS, 1999, 2 : 266 - 267
[36] Synthesis of carba analogues of 2′-deoxy-4′-C-(hydroxymethyl)nucleosides
Hrebabecky, H
Holy, A
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1999, 64 (09) : 1485 - 1496
[37] 2',3'-DIDEHYDRO-2',3'-DIDEOXY-5-CHLOROCYTIDINE IS A SELECTIVE ANTI-RETROVIRUS AGENT
BALZARINI, J
VANAERSCHOT, A
HERDEWIJN, P
DECLERCQ, E
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1989, 164 (03) : 1190 - 1197
[38] SYNTHESIS OF 3'-AZIDO-2',3'-DIDEOXY-6-METHYLURIDINE, 2',3'-DIDEOXY-6-METHYLURIDINE AND 2',3'-DIDEOXY-2',3'-DIDEHYDRO-6-METHYLURIDINE
HREBABECKY, H
HOLY, A
DECLERCQ, E
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1990, 55 (07) : 1801 - 1811
[39] SYNTHESIS OF (+/-)-2',3'-DIDEHYDRO-2',3'-DIDEOXY NUCLEOSIDES VIA A MODIFIED PRINS REACTION AND PALLADIUM(0) CATALYZED COUPLING
SAVILLESTONES, EA
LINDELL, SD
JENNINGS, NS
HEAD, JC
FORD, MJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10): : 2603 - 2604
[40] Darstellung von 2′,3′-Dideoxy-2′-hydroxymethyl-nucleosidenSynthesis of 2′,3′-dideoxy-2′-hydroxymethyl nucleosides
C. R. Noe
H. -P. Buchstaller
G. Haberhauer
A. Holzner
Monatshefte für Chemie / Chemical Monthly, 1997, 128 (5) : 509 - 527

← 1 2 3 4 5 →