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 [J].
ABUSHANAB, E ;
BESSODES, M ;
ANTONAKIS, K .
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 [J].
CHU, CK ;
AHN, SK ;
KIM, HO ;
BEACH, JW ;
ALVES, AJ ;
JEONG, LS ;
ISLAM, Q ;
VANROEY, P ;
SCHINAZI, RF .
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 [J].
COATES, JAV ;
CAMMACK, N ;
JENKINSON, HJ ;
MUTTON, IM ;
PEARSON, BA ;
STORER, R ;
CAMERON, JM ;
PENN, CR .
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 [J].
HERDEWIJN, P ;
BALZARINI, J ;
DECLERCQ, E ;
PAUWELS, R ;
BABA, M ;
BRODER, S ;
VANDERHAEGHE, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) :1270-1278
[9]   ASYMMETRIC-SYNTHESIS OF 1,3-DIOXOLANE PYRIMIDINE NUCLEOSIDES AND THEIR ANTI-HIV ACTIVITY [J].
KIM, HO ;
AHN, SK ;
ALVES, AJ ;
BEACH, JW ;
JEONG, LS ;
CHOI, BG ;
VANROEY, P ;
SCHINAZI, RF ;
CHU, CK .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) :1987-1995
[10]  
MARCH J, 1985, ADV ORG CHEM, P654