AN EXPEDITIOUS SYNTHESIS OF HOMOCHIRAL (R) 2-(9-PURINYL)BUTANE-1,4-DIOLS FROM (S) BUTANE-1,2,4-TRIOL

被引:10
作者
PERBOST, M [1 ]
LUCAS, M [1 ]
CHAVIS, C [1 ]
IMBACH, JL [1 ]
机构
[1] UNIV MONTPELLIER 2, CNRS, CHIM BIOORGAN LAB 488, CASE 008, F-34095 MONTPELLIER 5, FRANCE
关键词
D O I
10.1080/07328319208021193
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of (R) 2-(9-adenyl) and (R) 2-(9-guanyl)butane-1, 4-diols are described via an alkylation reaction of 6-chloropurine and N2-acetyl-O6-diphenylcarbamoyl guanine by (S) 1, 4-di-tert-butyldiphenylsilyloxybutane-2-ol under Mitsunobu conditions.
引用
收藏
页码:1529 / 1537
页数:9
相关论文
共 22 条
[1]  
ABELE G, 1991, Antiviral Chemistry and Chemotherapy, V2, P163
[2]   SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].
BORTHWICK, AD ;
BIGGADIKE, K .
TETRAHEDRON, 1992, 48 (04) :571-623
[3]   CHEMISTRY AND ANTIVIRAL ACTIVITIES OF ACYCLONUCLEOSIDES [J].
CHU, CK ;
CUTLER, SJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) :289-319
[4]   (+/-)-(1-ALPHA,2-BETA,3-ALPHA)-9-[2,3-BIS(HYDROXYMETHYL)-CYCLOBUTYL]GUANINE [(+/-)-BHCG OR SQ 33054] - A POTENT AND SELECTIVE INHIBITOR OF HERPESVIRUSES [J].
FIELD, AK ;
TUOMARI, AV ;
MCGEEVERRUBIN, B ;
TERRY, BJ ;
MAZINA, KE ;
HAFFEY, ML ;
HAGEN, ME ;
CLARK, JM ;
BRAITMAN, A ;
SLUSARCHYK, WA ;
YOUNG, MG ;
ZAHLER, R .
ANTIVIRAL RESEARCH, 1990, 13 (01) :41-52
[5]   ENANTIO-SELECTIVE AND DIASTEREO-SELECTIVE SYNTHESIS OF CARBOCYCLIC OXETANOCIN ANALOGS [J].
ICHIKAWA, Y ;
NARITA, A ;
SHIOZAWA, A ;
HAYASHI, Y ;
NARASAKA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (24) :1919-1921
[6]   SYNTHETIC ROUTES TO NUCLEOSIDE ANALOGS OF N-SUBSTITUTED 1,3-THIAZOLIDINES [J].
IWAKAWA, M ;
PINTO, BM ;
SZAREK, WA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (03) :326-335
[7]   SYNTHESIS OF SQ-32,829, A NEW NUCLEOSIDE ANTIVIRAL AGENT [J].
JACOBS, GA ;
TINO, JA ;
ZAHLER, R .
TETRAHEDRON LETTERS, 1989, 30 (50) :6955-6958
[8]   CARBOCYCLIC ANALOGS OF NUCLEOSIDES VIA MODIFIED MITSUNOBU REACTIONS [J].
JENNY, TF ;
PREVISANI, N ;
BENNER, SA .
TETRAHEDRON LETTERS, 1991, 32 (48) :7029-7032
[9]   SYNTHESIS OF METHYL 3-(N'-ALKYLUREIDO)-2-METHYL-2-PROPENOATES AND THEIR CYCLIZATION TO 3-ALKYL-5-METHYLURACILS [J].
LEDVINA, M ;
FARKAS, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1982, 47 (02) :676-688
[10]   CARBOCYCLIC NUCLEOSIDES [J].
MARQUEZ, VE ;
LIM, MI .
MEDICINAL RESEARCH REVIEWS, 1986, 6 (01) :1-40