PREPARATION OF C-(2-DEOXYHEX/PENT-1-ENOPYRANOSYL)HETEROCYCLES

被引：35

作者：

MAHMOUD, SH ^{[1
]}

SOMSAK, L ^{[1
]}

FARKAS, I ^{[1
]}

机构：

[1] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY

来源：

CARBOHYDRATE RESEARCH | 1994年 / 254卷

基金：

匈牙利科学研究基金会;

关键词：

D O I：

10.1016/0008-6215(94)84245-0

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：

Acetylated 1-cyanoglycals (2,6-anhydro-3-deoxyhept/hex-2-enononitriles) were prepared by direct elimination of acetic acid from the appropriate acetylated 2,6-anhydrohept/hexononitriles with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in aprotic solvents. Heterocyclisation of the cyano group of acetylated 1-cyano-D-galactal with 2-aminothiophenol led to 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)benzothiazole. Several 2-(per-O-acetylhexo/pentopyranosyl)benzothiazoles also gave 2-(per-O-acetyl-2-deoxyhex/pent-1-enopyranosyl)benzothiazoles with DBU. 3-(Per-O-acetylhexo/pentopyranosyl)-[1,2,4]triazolo[4,3-a]pyrimid rearranged with DBU to the corresponding acetylated 2-glycosyl-[1,2,4]triazolo[1,5-a]pyrimidines. By the reaction of 1-cyano-D-galactal with ammonium azide, 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1enopyranosyl)tetrazole was prepared and then transformed with carboxylic acid derivatives into 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranozyl)5-substituted-1,3,4-oxadiazoles.

引用

页码：91 / 104

页数：14

共 42 条

[1] SYNTHESIS OF C-NUCLEOSIDES .19. 2-L-RHAMNOPYRANOSYL[1,2,4]TRIAZOLO[1,5-A]PYRIDINE - 4' AND 3' OXIDATION-PRODUCTS SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].

ALLARD, P ;

DINH, TH ;

GOUYETTE, C ;

IGOLEN, J ;

CHERMANN, JC ;

BARRESINOUSSI, F .

JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (11) :1291-1297

[2]

BEPTISTELLA LHB, 1989, SYNTHESIS-STUTTGART, P436

[3]

Buchanan J.G., 1983, PROG CHEM ORG NATURA, V44, P243

[4] SYNTHESIS OF C-GLYCOSYLTETRAZOLES RELATED TO 3-DEOXY-D-ARABINO-HEPTULOSONIC ACID 7-PHOSPHATE (DAHP) - POTENTIAL INHIBITORS OF EARLY STEPS IN THE SHIKIMATE PATHWAY [J].

BUCHANAN, JG ;

CLELLAND, APW ;

JOHNSON, T ;

RENNIE, RAC ;

WIGHTMAN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (20) :2593-2601

[5] CONFORMATIONAL STUDIES OF D-GLYCALS BY H-1 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].

CHALMERS, AA ;

HALL, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (06) :728-732

[6] STRUCTURE OF 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL CYANIDE + SOME DERIVATIVES THEREFROM . SYNTHESIS OF 1-DEOXY-D-GALACTO-HEPTULOSE [J].

COXON, B ;

FLETCHER, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (05) :922-&

[7] UNCATALYZED AND CHORISMATE MUTASE CATALYZED CLAISEN REARRANGEMENTS OF 5,6-DIHYDROCHORISMATE AND 6-OXA-5,6-DIHYDROCHORISMATE [J].

DELANY, JJ ;

PADYKULA, RE ;

BERCHTOLD, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1394-1397

[8] INEFFECTIVENESS OF ANALOGS OF D-GALACTAL AS COMPETITIVE INHIBITORS OF, AND SUBSTRATES FOR, BETA-D-GALACTOSIDASE FROM ESCHERICHIA-COLI [J].

DETTINGER, HM ;

KURZ, G ;

LEHMANN, J .

CARBOHYDRATE RESEARCH, 1979, 74 (SEP) :301-307

[9] SYNTHESIS AND BIOLOGICAL EVALUATION OF 2-(2-DEOXY-D-ERYTHRO-PENT-1-ENOFURANOSYL)PYRIDINE C-NUCLEOSIDES [J].

DEVOS, E ;

ESMANS, EL ;

LEPOIVRE, JA ;

ALDERWEIRELDT, FC ;

DOMMISSE, RA ;

FRANCOIS, P ;

TOUILLAUX, R ;

BALZARINI, J ;

DECLERCQ, E .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1991, 10 (07) :1573-1598

[10]

DINH TH, 1976, J ORG CHEM, V41, P3124

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