A CONVENIENT METHOD FOR THE SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXY-NUCLEOSIDES

被引：0
|
作者：
DORLAND, E [1 ]
SERAFINOWSKI, P [1 ]
机构：
[1] INST CANC RES, DRUG DEV SECT, COTSWOLD RD, SUTTON SM2 5NG, SURREY, ENGLAND
来源：
SYNTHESIS-STUTTGART | 1992年 / 05期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
9-(2,3-Dideoxy-beta-D-glyceropent-2-enofuranosyl)adenine (2',3'-didehydro-2',3'-dideoxyadenosine, 9a), 9-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)hypoxanthine (2',3'-didehydro-2',3'-dideoxyinosine, 9b) and 4-amino-7-(2,3-dideoxy-beta-D-glyceropent-2-eno-furanosyl)pyrrolo[2,3-d]pyrimidine (2',3'-didehydro-2',3'-dideoxy-tubercidin, 9c) were prepared via a free radical beta-elimination of bromo and phenoxy(thiocarbonyl) leaving groups from appropriate 5'-O-(2-acetoxyisobutyryl)-2'(3')-phenoxy(thiocarbonyl)-3'(2')-bromo derivatives 6, 7 of adenosine (1a), inosine (1b) and tubercidin (1c) with tributyltin hydride and subsequent deprotection of the resulting 5'-O-(2-acetoxyisobutyryl)-2',3'-didehydro-2',3'-dideoxy-nucleosides 8a, Sb and 8c, respectively.
引用
收藏
页码：477 / 481
页数：5
相关论文
共 50 条
  • [21] SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXY-2'-C- METHYLSUBSTITUTED NUCLEOSIDES USING A NOVEL SN2' TYPE REACTION
    IONNIDIS, P
    CLASSON, B
    SAMUELSSON, B
    KVARNSTROM, I
    NUCLEOSIDES & NUCLEOTIDES, 1993, 12 (05): : 449 - 462
  • [22] CONFORMATIONAL-ANALYSIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYPYRIMIDINE NUCLEOSIDES
    VANROEY, P
    TAYLOR, EW
    CHU, CK
    SCHINAZI, RF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) : 5365 - 5371
  • [23] SYNTHESIS AND ANTIVIRAL EVALUATION OF ENANTIOMERIC 2',3'-DIDEOXY-2',3'-DIDEOXY-4'-THIONUCLEOSIDES AND 2',3'-DIDEHYDRO-2',3'-DIDEOXY-4'-THIONUCLEOSIDES
    YOUNG, RJ
    SHAWPONTER, S
    THOMSON, JB
    MILLER, JA
    CUMMING, JG
    PUGH, AW
    RIDER, P
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (22) : 2599 - 2604
  • [24] Synthesis, antiviral activity, and mechanism of drug resistance of D- and L-2′,3′-didehydro-2′,3′-dideoxy-2′-fluorocarbocyclic nucleosides
    Wang, JN
    Jin, YH
    Rapp, KL
    Bennett, M
    Schinazi, RF
    Chu, CK
    JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (11) : 3736 - 3748
  • [25] SYNTHESIS OF 2′-DEOXY-4′-C-HYDROXYMETHYL-4′-THIORIBONUCLEOSIDES AND THEIR 2′,3′-DIDEOXY AND 2′,3′-DIDEHYDRO-2′,3′-DIDEOXY ANALOGUES
    Nokami, Junzo
    Mae, Masayuki
    Fukutake, Satoshi
    Ubuka, Tomoyuki
    Yamada, Mitsuhiro
    HETEROCYCLES, 2008, 76 (02) : 1337 - 1360
  • [26] Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′-selenonucleosides
    Tosh, Dilip K.
    Choi, Won Jun
    Kim, Hea Ok
    Lee, Yoonji
    Pal, Shantanu
    Hou, Xiyan
    Choi, Jungwon
    Choi, Sun
    Jeong, Lak Shin
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (11): : 4259 - 4262
  • [27] NEW STRATEGIES IN THE SYNTHESIS OF 3'-AZIDO-2',3'-DIDEOXY-NUCLEOSIDES WITH FURANOSE CONFIGURATION
    WENGEL, J
    LAU, J
    WALCZAK, K
    PEDERSEN, EB
    NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (1-3): : 405 - 408
  • [28] NEW SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES
    ABDELMEGIED, AES
    HANSEN, P
    PEDERSEN, EB
    NIELSEN, CM
    ACTA CHEMICA SCANDINAVICA, 1991, 45 (10): : 1060 - 1063
  • [29] Synthesis of novel 2′,3′-didehydro-2′,3′-dideoxynucleoside
    Yadava, VS
    ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (04) : 2857 - 2859
  • [30] NUCLEOSIDES .4. SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYDORIDOSINE AND 2',3'-DIDEOXYDORIDOSINE AS POTENTIAL ANTIHYPERTENSIVE AGENTS
    CHERN, JW
    LIN, GS
    CHEN, CS
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1992, 39 (04) : 347 - 350
12345