Synthesis of 9-[2',3'-dideoxy-2',3'-bis-C-hydroxymethyl-alpha-L-threofuranosyl] adenine and its 4'-thio analog as potential antiviral agents

被引:13
|
作者
Kikuchi, Y
Kurata, H
Nishiyama, S
Yamamura, S
Kato, K
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
关键词
D O I
10.1016/S0040-4039(97)01035-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantiomerically pure synthesis or 9-[2',3'-dideoxy-2-'3'-bis-C-hydrosymethyl-alpha-L-threorunnosyl]adenine and its 4'-thio analog was achieved via coupling or silylated 6-chloropurine with 1-O-acetyfuranose derivative 17 and its 4'-thio analog 24, respectively, prepared from (+)-diethyl L-tartrate. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4795 / 4798
页数:4
相关论文
共 50 条
  • [41] Synthesis of 3-fluoro-2′,3′-dideoxy-2′,3′-didehydro-4′-ethynyl-D- and -L-furanosyl nucleosides
    Chen, X
    Zhou, W
    Schinazi, RF
    Chu, CK
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18): : 6034 - 6041
  • [42] SYNTHESIS AND BIOLOGICAL EVALUATION OF 2',3'-DIDEOXY-L-PYRIMIDINE NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS AGAINST HIV AND HBV
    LIN, TS
    LUO, MZ
    LIU, MC
    PAI, SB
    DUTSCHMAN, GE
    CHENG, YC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 31 - MEDI
  • [43] Synthesis and biological evaluation of 9-[2-fluoro-4-hydroxy-3-hydroxymethyl-2-butenyl]adenine and its related compounds as open-chain analogues of neplanocin A
    Choi, MH
    Kim, HD
    ARCHIVES OF PHARMACAL RESEARCH, 1997, 20 (05) : 501 - 506
  • [44] Synthesis and biological evaluation of 9-[2-fluoro-4-hydroxy-3-hydroxymethyl-2-butenyl]adenine and its related compounds as open-chain analogues of neplanocin A
    Myung-Hee Choi
    Hee-Doo Kim
    Archives of Pharmacal Research, 1997, 20 : 501 - 506
  • [45] OXIDATIVE-DEGRADATION OF L-ASCORBIC-ACID ACETALS TO 2',3'-DIDEOXY-3'-OXARIBOFURANOSIDES - SYNTHESIS OF ENANTIOMERICALLY PURE 2',3'-DIDEOXY-3'-OXACYTIDINE STEREOISOMERS AS POTENTIAL ANTIVIRAL AGENTS
    BELLEAU, BR
    EVANS, CA
    TSE, HLA
    JIN, HL
    DIXIT, DM
    MANSOUR, TS
    TETRAHEDRON LETTERS, 1992, 33 (46) : 6949 - 6952
  • [46] POTENTIAL ANTICANCER AGENTS .39. AN ALTERNATIVE SYNTHESIS OF 9-(2',3'-ANHYDRO-BETA-D-RIBOFURANOSYL)ADENINE
    BENITEZ, A
    CREWS, OP
    GOODMAN, L
    BAKER, BR
    JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (11): : 1946 - 1950
  • [47] ENANTIOSPECIFIC SYNTHESIS OF [(2'S, 3'S)-BIS(HYDROXYMETHYL)AZETIDIN-1-YL] PYRIMIDINE NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS
    HOSONO, F
    NISHIYAMA, S
    YAMAMURA, S
    IZAWA, T
    KATO, K
    TERADA, Y
    TETRAHEDRON, 1994, 50 (47) : 13335 - 13346
  • [48] Synthesis of carbocyclic 2',3'-dideoxy-2'-fluoro-3'-C-hydroxymeth yl nucleoside analogues as potential inhibitors of HIV and HSV
    Wachtmeister, J.
    Classon, B.
    Samuelsson, B.
    Kvarnstroem, I.
    Tetrahedron, 53 (05):
  • [49] Synthesis and potent anti-HIV activity of L-2′,3′-didehydro-2′,3′-dideoxy-2′-fluoro-4′-thiocytidine
    Choi, Y
    Choo, H
    Chong, Y
    Lee, S
    Olgen, S
    Schinazi, RF
    Chu, CK
    ORGANIC LETTERS, 2002, 4 (02) : 305 - 307
  • [50] Synthesis and anti-HIV activity of L-2′,3′-didehydro-2′,3′-dideoxy-2′-fluoro-4′-thiocytidine.
    Choi, Y
    Choo, H
    Chong, YH
    Lee, S
    Olgen, S
    Schinazi, RF
    Chu, CK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U165 - U165