Synthesis of 2′,3′-dideoxy-3′-C-(hydroxymethyl)-4′-thiopentofuranosyl nucleosides as potential antiviral agent

被引：15
|
作者：
Ichikawa, E
Yamamura, S
Kato, K [1 ]
机构：
[1] Nippon Kayaku Co Ltd, Pharmaceut Grp, Res Labs, Kita Ku, Tokyo 115, Japan
[2] Keio Univ, Fac Sci & Technol, Dept Chem, Yokohama, Kanagawa 223, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 08期
关键词：
antivirals; nucleosides;
D O I：
10.1016/S0960-894X(99)00142-0
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
2-O-Acetyl-2,3-dideoxy-3-C-(hydroxymethy)-4-thiofuranose derivative was synthesized from (S, S)-1,4-bis(benzyloxy)-2,3-epoxybutane derived from (+)-diethyl L-tartrate and the enantiomerically pure (E)-5-(2-bromovinyl)- 1-[2', 3'-dideoxy-3'-C-(hydroxymethyl)-beta-D-4'-thiopentofuranosyl] uracil 4 was obtained via coupling of silylated uracil followed by palladium-mediated coupling of methyl acrylate. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1113 / 1114
页数：2
相关论文
共 50 条
  • [1] SYNTHESIS OF 2',3'-DIDEOXY-3'-C-(HYDROXYMETHYL)-4'-THIONUCLEOSIDES AS POTENTIAL INHIBITORS OF HIV
    BRANALT, J
    KVARNSTROM, I
    NIKLASSON, G
    SVENSSON, SCT
    CLASSON, B
    SAMUELSSON, B
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07): : 1783 - 1788
  • [2] SYNTHESIS OF 2',3'-DIDEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES AS POTENTIAL INHIBITORS OF HIV
    SVANSSON, L
    KVARNSTROM, I
    CLASSON, B
    SAMUELSSON, B
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09): : 2993 - 2997
  • [3] 2 SYNTHETIC ROUTES TO 2',3'-DIDEOXY-3'-C-(HYDROXYMETHYL)-4'-THIONUCLEOSIDES
    MANN, J
    TENCH, AJ
    WEYMOUTH, AC
    SHAWPONTER, S
    YOUNG, RJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (06): : 677 - 681
  • [4] Synthesis and antiviral evaluation of α-D-2′,3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides
    Yamada, Kohei
    Hayakawa, Hiroyuki
    Sakata, Shinji
    Ashida, Noriyuki
    Yoshimura, Yuichi
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (20) : 6013 - 6016
  • [5] Synthesis and HIV inhibition activity of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides
    LeeRuff, E
    Ostrowski, M
    Ladha, A
    Stynes, DV
    Vernik, I
    Jiang, JL
    Wan, WQ
    Ding, SF
    Joshi, S
    JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) : 5276 - 5280
  • [6] SYNTHESIS OF SOME PURINE CARBOCYCLIC ISOSTERES OF 2',3'-DIDEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES AS POTENTIAL INHIBITORS OF HIV
    JANSON, M
    SVANSSON, L
    SVENSSON, SCT
    KVARNSTROM, I
    CLASSON, B
    SAMUELSSON, B
    NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (10): : 1739 - 1747
  • [7] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF CARBOCYCLIC 2',3'-DIDEOXY-3'-FLUORO NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS
    NAKAYAMA, T
    MATSUMURA, Y
    MORIZAWA, Y
    YASUDA, A
    UCHIDA, K
    TAKASE, H
    MURAKAMI, Y
    ATARASHI, S
    IKEUCHI, T
    OSADA, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (02) : 183 - 187
  • [8] SYNTHESIS OF 2',3'-DIDEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES HAVING THE L-CONFIGURATION AS POTENTIAL INHIBITORS OF HIV
    KVARNSTROM, I
    SVANSSON, L
    SVENSSON, C
    SVENSSON, SCT
    CLASSON, B
    SAMUELSSON, B
    NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (07): : 1367 - 1370
  • [9] Synthesis and antiviral evaluation of 4'-hydroxymethyl-2',3'-dideoxy-3'thianucleosides and their cyclic monophosphates
    Chao, Q
    Nair, V
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (09) : 1199 - 1202
  • [10] Synthesis of (±)-2′,3′-dideoxy-3′-fluoroapiosylpyrimide nucleosides
    Ahn, SK
    Kim, D
    Son, HJ
    Jeong, BS
    Hong, RK
    Kim, BY
    Kim, EN
    Chung, KH
    Kim, JW
    CHEMICAL COMMUNICATIONS, 1998, (09) : 967 - 968
12345