SYNTHESIS OF THYMINE NUCLEOSIDES DERIVED FROM 1-DEOXY-D-PSICOFURANOSE

被引:20
作者
FAIVREBUET, V [1 ]
GROUILLER, A [1 ]
DESCOTES, G [1 ]
机构
[1] UNIV LYON 1,CHIM ORGAN LAB 2,CNRS,URA 463,BAT 308,43 BLVD 11 NOVEMBRE 1918,F-69622 VILLEURBANNE,FRANCE
来源
NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 09期
关键词
D O I
10.1080/07328319208021356
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 use of D-(+)-ribonic gamma-lactone 1a,b as a chiral synthon leads to an efficient synthesis of the ketose 1-deoxy-D-psicofuranose 2a,b. Condensation of the corresponding acetyl derivative 3a,b with silylated thymine, followed by deprotection of 4a,b, affords an anomeric mixture of ketosyl nucleoside 6 (predominately the beta-anomer) in an improved overall yield of 49 %.
引用
收藏
页码:1651 / 1660
页数:10
相关论文
共 15 条
[1]   SYNTHESIS AND EVALUATION OF A SERIES OF 1-(3-ALKYL-2,3-DIDEOXY-ALPHA,BETA-D-ERYTHRO-PENTOFURANOSYL)THYMINES [J].
AGYEIAYE, K ;
BAKER, DC .
CARBOHYDRATE RESEARCH, 1988, 183 (02) :261-275
[2]  
BIEG T, 1985, SYNTHESIS-STUTTGART, V1, P76
[3]   DIFFERENTIALLY PROTECTED RIBOFURANOID GLYCALS [J].
CHENG, JCY ;
HACKSELL, U ;
DAVES, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) :2778-2780
[4]  
FAIVREBUET V, 1992, NUCLEOSIDES NUCLEOTI, V11
[5]   GENERAL-SYNTHESIS OF IMIDAZOLE C-NUCLEOSIDES FROM CARBOHYDRATE ADDUCTS OF DIAMINOMALEONITRILE [J].
FERRIS, JP ;
BADESHA, SS ;
REN, WY ;
HUANG, HC ;
SORCEK, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) :110-112
[6]  
GROUILLER A, 1988, NUCLEOS NUCLEOT, V7, P675
[7]  
HREBABECKY H, 1972, COLLECT CZECH CHEM C, V37, P2059
[8]   DETERMINATION OF ANOMERIC CONFIGURATION OF D-RIBOFURANOSYL NUCLEOSIDES BY PMR SPECTROSCOPY [J].
IMBACH, JL .
ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, 1975, 255 (AUG8) :177-184
[9]   SYNTHESIS OF THE DIDEOXYNUCLEOSIDES DDC AND CNT FROM GLUTAMIC-ACID, RIBONOLACTONE, AND PYRIMIDINE-BASES [J].
OKABE, M ;
SUN, RC ;
TAM, SYK ;
TODARO, LJ ;
COFFEN, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4780-4786
[10]  
PAUKIEWIEZ KW, 1988, J ORG CHEM, V53, P3473