A REINVESTIGATION OF THE SYNTHESIS OF 4-THIO-PENTOFURANOSIDES FOR FURTHER NUCLEOSIDIC SYNTHESIS

被引:13
作者
BELLON, L [1 ]
LEYDIER, C [1 ]
BARASCUT, JL [1 ]
IMBACH, JL [1 ]
机构
[1] UNIV MONTPELLIER 2,CHIM BIOORGAN LAB,CNRS,URA 488,CASE 008,PL E BATAILLON,F-34095 MONTPELLIER 5,FRANCE
来源
NUCLEOSIDES & NUCLEOTIDES | 1993年 / 12卷 / 08期
关键词
D O I
10.1080/07328319308018555
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
We demonstrate that the procedure of Huang and Hui(4), applied to the D-ribose and involving Ph3P/12/Imidazole reagent system do not lead to the desired 4-thio-D-ribofuranoside derivative but gives its diastereoisomer 4-thio-L-lyxofuranoside derivative 4.
引用
收藏
页码:847 / 852
页数:6
相关论文
共 11 条
[1]   2,3,5-TRI-O-BENZYL-D-RIBOSYL AND -L-ARABINOSYL BROMIDES [J].
BARKER, R ;
FLETCHER, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4605-&
[2]   EFFECT OF ACYCLIC PYRIMIDINES RELATED TO 9-[(1,3-DIHYDROXY-2-PROPOXY)METHYL]GUANINE ON HERPESVIRUSES [J].
BEAUCHAMP, LM ;
SERLING, BL ;
KELSEY, JE ;
BIRON, KK ;
COLLINS, P ;
SELWAY, J ;
LIN, JC ;
SCHAEFFER, HJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) :144-149
[3]   EFFICIENT SYNTHESIS OF 4-THIO-D-RIBOFURANOSE AND SOME 4'-THIORIBONUCLEOSIDES [J].
BELLON, L ;
BARASCUT, JL ;
IMBACH, JL .
NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (08) :1467-1479
[4]   4'-THIO-OLIGO-BETA-D-RIBONUCLEOTIDES - SYNTHESIS OF BETA-4'-THIO-OLIGOURIDYLATES, NUCLEASE RESISTANCE, BASE-PAIRING PROPERTIES, AND INTERACTION WITH HIV-1 REVERSE-TRANSCRIPTASE [J].
BELLON, L ;
BARASCUT, JL ;
MAURY, G ;
DIVITA, G ;
GOODY, R ;
IMBACH, JL .
NUCLEIC ACIDS RESEARCH, 1993, 21 (07) :1587-1593
[5]   SUGAR MODIFIED OLIGONUCLEOTIDES - SYNTHESIS, NUCLEASE RESISTANCE AND BASE-PAIRING OF OLIGODEOXYNUCLEOTIDES CONTAINING 1-(4'-THIO-BETA-D-RIBOFURANOSYL)-THYMINE [J].
BELLON, L ;
MORVAN, F ;
BARASCUT, JL ;
IMBACH, JL .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1992, 184 (02) :797-803
[6]   INTRA-MOLECULAR CYCLIZATION OF PENTOSE AND HEXOSE DITHIO-ACETALS [J].
BLUMBERG, K ;
FUCCELLO, A ;
VANES, T .
CARBOHYDRATE RESEARCH, 1979, 70 (02) :217-232
[7]   STANNYLENE DIRECTED SELECTIVE ACYLATION OF SOME OPEN-CHAIN L-ARABINOSE DERIVATIVES [J].
BREDENKAMP, MW ;
HOLZAPFEL, CW ;
SWANEPOEL, AD .
TETRAHEDRON LETTERS, 1990, 31 (19) :2759-2762
[8]  
DYSON MR, 1991, CARBOHYD RES, V216, P237
[9]   NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION .2. [J].
GAREGG, PJ ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2866-2869
[10]   STUDIES ON TOTAL SYNTHESIS OF OLIVOMYCINS [J].
HATCH, RP ;
SHRINGARPURE, J ;
WEINREB, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4172-4177