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

被引:36
作者
BELLEAU, BR [1 ]
EVANS, CA [1 ]
TSE, HLA [1 ]
JIN, HL [1 ]
DIXIT, DM [1 ]
MANSOUR, TS [1 ]
机构
[1] BIOCHEM PHARMA INC,531 BLVD PRAIRIES,LAVAL H7V 1B7,QUEBEC,CANADA
关键词
D O I
10.1016/S0040-4039(00)60903-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically pure 2',3'-dideoxy-3'-oxacytidine nucleoside analogues were synthesized from L-ascorbic acid in eight steps and good overall yield.
引用
收藏
页码:6949 / 6952
页数:4
相关论文
共 16 条
  • [1] PRACTICAL ENANTIOSPECIFIC SYNTHESES OF (+) ERYTHRO-9-(2S-HYDROXY-3R-NONYL) ADENINE
    ABUSHANAB, E
    BESSODES, M
    ANTONAKIS, K
    [J]. TETRAHEDRON LETTERS, 1984, 25 (35) : 3841 - 3844
  • [2] ABUSHANAB E, 1988, J ORG CHEM, V53, P2599
  • [3] BELLEAU B, 1989, 5TH INT C AIDS MONTR, P515
  • [4] ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE (-)-(1'R,4'R)-DIOXOLANE-THYMINE AND ITS ANTI-HIV ACTIVITY
    CHU, CK
    AHN, SK
    KIM, HO
    BEACH, JW
    ALVES, AJ
    JEONG, LS
    ISLAM, Q
    VANROEY, P
    SCHINAZI, RF
    [J]. TETRAHEDRON LETTERS, 1991, 32 (31) : 3791 - 3794
  • [5] THE SEPARATED ENANTIOMERS OF 2'-DEOXY-3'-THIACYTIDINE (BCH-189) BOTH INHIBIT HUMAN-IMMUNODEFICIENCY-VIRUS REPLICATION INVITRO
    COATES, JAV
    CAMMACK, N
    JENKINSON, HJ
    MUTTON, IM
    PEARSON, BA
    STORER, R
    CAMERON, JM
    PENN, CR
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (01) : 202 - 205
  • [6] EMMONS CHH, 1991, TETRAHEDRON-ASYMMETR, V2, P359
  • [7] 3'-SUBSTITUTED 2',3'-DIDEOXYNUCLEOSIDE ANALOGS AS POTENTIAL ANTI-HIV (HTLV-III/LAV) AGENTS
    HERDEWIJN, P
    BALZARINI, J
    DECLERCQ, E
    PAUWELS, R
    BABA, M
    BRODER, S
    VANDERHAEGHE, H
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) : 1270 - 1278
  • [9] ASYMMETRIC-SYNTHESIS OF 1,3-DIOXOLANE PYRIMIDINE NUCLEOSIDES AND THEIR ANTI-HIV ACTIVITY
    KIM, HO
    AHN, SK
    ALVES, AJ
    BEACH, JW
    JEONG, LS
    CHOI, BG
    VANROEY, P
    SCHINAZI, RF
    CHU, CK
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) : 1987 - 1995
  • [10] MARCH J, 1985, ADV ORG CHEM, P654