DIVERGENT ASYMMETRIC SYNTHESES OF DIOXOLANE NUCLEOSIDE ANALOGS

被引:14
作者
EVANS, CA [1 ]
DIXIT, DM [1 ]
SIDDIQUI, MA [1 ]
JIN, HL [1 ]
TSE, HLA [1 ]
CIMPOIA, A [1 ]
BEDNARSKI, K [1 ]
BREINING, T [1 ]
MANSOUR, TS [1 ]
机构
[1] BIOCHEM THERAPEUT INC,531 PRAIRIES BLVD,LAVAL H7V 1B7,PQ,CANADA
关键词
D O I
10.1016/S0957-4166(00)80092-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Oxidative degradation of benzyloxymethylacetals derived from D-mannitol or L-ascorbic acid provides dioxolane intermediate 6 and 7 useful in the synthesis of all the stereoisomers of dioxolane nucleoside analogues.
引用
收藏
页码:2319 / 2322
页数:4
相关论文
共 12 条
[1]  
BELLEAU B, 1989, 5TH INT C AIDS MONTR, P515
[2]   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 [J].
BELLEAU, BR ;
EVANS, CA ;
TSE, HLA ;
JIN, HL ;
DIXIT, DM ;
MANSOUR, TS .
TETRAHEDRON LETTERS, 1992, 33 (46) :6949-6952
[3]   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
[4]  
DIMARCO MP, 1993, J CHROMATOGR
[5]  
EMMONS CHH, 1991, TETRAHEDRON-ASYMMETR, V2, P359
[6]   UNEXPECTED EFFECTS OF LEWIS-ACIDS IN THE SYNTHESIS OF OPTICALLY PURE 2'-DEOXY-3'-OXACYTIDINE NUCLEOSIDE ANALOGS [J].
JIN, HL ;
TSE, HLA ;
EVANS, CA ;
MANSOUR, TS ;
BEELS, CM ;
RAVENSCROFT, P ;
HUMBER, DC ;
JONES, MF ;
PAYNE, JJ ;
RAMSAY, MVJ .
TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :211-214
[7]   1,3-DIOXOLANYLPURINE NUCLEOSIDES (2R,4R) AND (2R,4S) WITH SELECTIVE ANTI-HIV-1 ACTIVITY IN HUMAN-LYMPHOCYTES [J].
KIM, HO ;
SCHINAZI, RF ;
NAMPALLI, S ;
SHANMUGANATHAN, K ;
CANNON, DL ;
ALVES, AJ ;
JEONG, LS ;
BEACH, JW ;
CHU, CK .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (01) :30-37
[8]   POTENT ANTI-HIV AND ANTI-HBV ACTIVITIES OF (-)-L-BETA-DIOXOLANE-C AND (+)-L-BETA-DIOXOLANE-T AND THEIR ASYMMETRIC SYNTHESES [J].
KIM, HO ;
SHANMUGANATHAN, K ;
ALVES, AJ ;
JEONG, LS ;
BEACH, JW ;
SCHINAZI, RF ;
CHANG, CN ;
CHENG, YC ;
CHU, CK .
TETRAHEDRON LETTERS, 1992, 33 (46) :6899-6902
[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]   (+/-)-DIOXOLANE-T ((+/-)-1-[(2-BETA, 4-BETA)-2-(HYDROXYMETHYL)-4-DIOXOLANYL]THYMINE) - A NEW 2',3'-DIDEOXYNUCLEOSIDE PROTOTYPE WITH INVITRO ACTIVITY AGAINST HIV [J].
NORBECK, DW ;
SPANTON, S ;
BRODER, S ;
MITSUYA, H .
TETRAHEDRON LETTERS, 1989, 30 (46) :6263-6266