Nucleosides and nucleotides .139. Stereoselective synthesis of (2'S)-2'-C-alkyl-2'-deoxyuridines

被引：8

作者：

Iino, T ^{[1
]}

Shuto, S ^{[1
]}

Matsuda, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN

来源：

NUCLEOSIDES & NUCLEOTIDES | 1996年 / 15卷 / 1-3期

关键词：

D O I：

10.1080/07328319608002378

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A synthetic method for (2'S)-2'-C-alkyl-2'-deoxyuridines (9) has been described. Catalytic hydrogenation of 1-[2-C-alkynyl-2-O-methoxalyl-3,5-O-TIPDS-beta-D-arabino-pentofuranosyl]uracils (5) gave 1-[2-C-(2-alkyl)-2-O-methoxalyl-3,5-O-TIPDS-beta-D-arabino-pentofuranosyl]uracils (4) as a major product, which were then subjected to the radical deoxygenation, affording (2'S)-2'-alkyl-2'-deoxy-3',5'-O-TIPDS-uridines (7) along with a small amount of their 2'R epimers.

引用

页码：169 / 181

页数：13

共 17 条

[1] NUCLEOSIDES AND NUCLEOTIDES .128. (2'S)-2'-DEOXY-2'-C-METHYL-5-IODOURIDINE (SMIU) AS A NOVEL POTENT ANTI-HERPES VIRUS AGENT
AWANO, H
SHUTO, S
BABA, M
KIRA, T
SHIGETA, S
MATSUDA, A
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (02) : 367 - 370
[2] NUCLEOSIDES AND NUCLEOTIDES .122. 2'-C-CYANO-2'-DEOXY-1-BETA-D-ARABINOFURANOSYLCYTOSINE AND ITS DERIVATIVES - A NEW CLASS OF NUCLEOSIDE WITH A BROAD ANTITUMOR SPECTRUM
AZUMA, A
NAKAJIMA, Y
NISHIZONO, N
MINAKAWA, N
SUZUKI, M
HANAOKA, K
KOBAYASHI, T
TANAKA, M
SASAKI, T
MATSUDA, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (26) : 4183 - 4189
[3] HAYAKAWA H, 1987, CHEM PHARM BULL, V35, P2605
[4] NUCLEOSIDES AND NUCLEOTIDES .134. SYNTHESIS OF 2'-C-ALKYNYL-2'-DEOXY-1-BETA-D-ARABINOFURANOSYLPYRIMIDINES VIA RADICAL DEOXYGENATION OF TERT-PROPARGYL ALCOHOLS IN THE SUGAR MOIETY
IINO, T
YOSHIMURA, Y
MATSUDA, A
[J]. TETRAHEDRON, 1994, 50 (35) : 10397 - 10406
[5] NUCLEOSIDES AND NUCLEOTIDES .132. SYNTHESIS AND BIOLOGICAL EVALUATIONS OF RING-EXPANDED OXETANOCIN ANALOGS - PURINE AND PYRIMIDINE ANALOGS OF 1,4-ANHYDRO-2-DEOXY-D-ARABITOL AND 1,4-ANHYDRO-2-DEOXY-3-HYDROXYMETHYL-D-ARABITOL
KAKEFUDA, A
SHUTO, S
NAGAHATA, T
SEKI, J
SASAKI, T
MATSUDA, A
[J]. TETRAHEDRON, 1994, 50 (34) : 10167 - 10182
[6] MATSUDA A, 1987, CHEM PHARM BULL, V35, P3967
[7] NUCLEOSIDES AND NUCLEOTIDES .94. RADICAL DEOXYGENATION OF TERT-ALCOHOLS IN 1-(2-C-ALKYLPENTOFURANOSYL)PYRIMIDINES - SYNTHESIS OF (2'S)-2'-DEOXY-2'-C-METHYLCYTIDINE, AN ANTILEUKEMIC NUCLEOSIDE
MATSUDA, A
TAKENUKI, K
SASAKI, T
UEDA, T
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) : 234 - 239
[8] MATSUDA A, 1993, NUCLEOSIDES AND NUCLEOTIDES AS ANTITUMOR AND ANTIVIRAL AGENTS, P1
[9] NUCLEOSIDES AND NUCLEOTIDES .100. 2'-C-CYANO-2'-DEOXY-1-BETA-D-ARABINOFURANOSYLCYTOSINE (CNDAC) - DESIGN OF A POTENTIAL MECHANISM-BASED DNA-STRAND-BREAKING ANTINEOPLASTIC NUCLEOSIDE
MATSUDA, A
NAKAJIMA, Y
AZUMA, A
TANAKA, M
SASAKI, T
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) : 2917 - 2919
[10] MATSUDA A, 1988, CHEM PHARM BULL, V36, P945

← 1 2 →