SYNTHESIS OF 2-(BETA-D-RIBOFURANOSYL)THIAZOLE-4-CARBOXAMIDE 5'-PHOSPHATE ISOSTERES

被引：9

作者：

ANDRES, JI ^{[1
]}

GARCIALOPEZ, T ^{[1
]}

DELASHERAS, FG ^{[1
]}

MENDEZCASTRILLON, PP ^{[1
]}

机构：

[1] INST QUIM MED, JUAN CIERVA 3, E-28006 MADRID, SPAIN

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 1986年 / 5卷 / 04期

关键词：

D O I：

10.1080/07328318608068683

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 syntheses of 5''-O-sulfamoyl and 5''-O-carbamoyl tiazofurin (9 and 12) are described. One pot reaction of 2'',3''-O-isopropylidene-tiazofurin (7) with hexabutyldistannoxane and sulfamoyl chloride gave the corresponding 5''-O-sulfamoyl ester, which was deprotected to yield 9. Compound 7 reacted with phenyl chloroformate to give the 5''-O-carbophenoxy derivative which on treatment with ammonium hydroxide followed by deisopropylidenation afforded 12. Improvements on the synthetic route to the starting tiazofurin are also reported.

引用

页码：423 / 429

页数：7

共 50 条

[1] SYNTHESIS OF 2-(3-DEOXY-BETA-D-ERYTHROPENTOFURANOSYL)-THIAZOLE-4-CARBOXAMIDE (3'-DEOXYTIAZOFURIN)
BAUR, RH
BAKER, DC
NUCLEOSIDES & NUCLEOTIDES, 1984, 3 (01): : 77 - 89
[2] SYNTHESIS OF 4-SUBSTITUTED 5-AMINO-2-(BETA-D-RIBOFURANOSYL)THIAZOLES AND 4-SUBSTITUTED 5-AMINO-2-(BETA-D-RIBOFURANOSYL)SELENAZOLES AND THEIR RESPECTIVE CONVERSION INTO 2-(BETA-D-RIBOFURANOSYL)THIAZOLO[5,4-D]PYRIMIDINES AND 2-(BETA-D-RIBOFURANOSYL)SELENAZOLO[5,4-D]PYRIMIDINES - A NEW SYNTHESIS OF TIAZOFURIN AND SELENAZOFURINN
HENNEN, WJ
HINSHAW, BC
RILEY, TA
WOOD, SG
ROBINS, RK
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10): : 1741 - 1746
[3] SYNTHESIS OF 2-(4'-AMINO-4'-DEOXY-BETA-D-RIBOFURANOSYL)THIAZOLE-4-CARBOXAMIDE, A CARBON-LINKED NUCLEOSIDE WITH A FREE PYRROLIDINE SUGAR
KINI, GD
HENNEN, WJ
ROBINS, RK
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (23): : 4436 - 4439
[4] Synthesis of 2-(3′-azido- and 3′-amino-3′-deoxy-β-D-ribofuranosyl)thiazole-4-carboxamide
Liang, CW
Kim, MJ
Jeong, LS
Chun, MW
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (11): : 2039 - 2048
[5] SYNTHESIS OF 2-(BETA-D-RIBOFURANOSYL)[1,3,5]TRIAZINES
RILEY, TA
HENNEN, WJ
DALLEY, NK
WILSON, BE
ROBINS, RK
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (06) : 1709 - 1714
[6] SYNTHESIS OF 5-BETA-D-RIBOFURANOSYL-1,3-THIAZOLE-2-CARBOXAMIDE - THIAZOLE ANALOG OF RIBAVIRIN
VANEK, T
FARKAS, J
GUT, J
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1979, 44 (04) : 1339 - 1342
[7] POSSIBLE MECHANISM OF ACTION OF 2-BETA-D-RIBOFURANOSYL THIAZOLE-4-CARBOXAMIDE IN CHINESE-HAMSTER OVARY CELLS
KUTTAN, R
LAI, MM
SAUNDERS, PP
PROCEEDINGS OF THE AMERICAN ASSOCIATION FOR CANCER RESEARCH, 1982, 23 (MAR): : 218 - 218
[8] SYNTHESIS OF 5-(BETA-D-RIBOFURANOSYL)-1,2,4-OXADIAZOLE-3-CARBOXAMIDE
HENNEN, WJ
ROBINS, RK
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (06) : 1747 - 1748
[9] Syntheses of [2-H-2]-5-ethynyl-1-(beta-D-ribofuranosyl)imidazole-4-carboxamide and 5-ethynyl-1-([5-H-3]-beta-D-ribofuranosyl)imidazole-4-carboxamide (EICAR)
Minakawa, N
Matsuda, A
Xia, ZP
Wiebe, LI
Knaus, EE
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1996, 38 (09): : 809 - 824
[10] HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC DETERMINATION OF 2-BETA-D RIBOFURANOSYL THIAZOLE-4-CARBOXAMIDE IN URINE AND PLASMA
CHANDRASEKARAN, B
ARDALAN, B
PROCEEDINGS OF THE AMERICAN ASSOCIATION FOR CANCER RESEARCH, 1983, 24 (MAR): : 291 - 291

← 1 2 3 4 5 →