GENERAL-SYNTHESIS OF CARBANUCLEOSIDES VIA REGIOSPECIFIC EPOXIDE OPENING BY THE AGLYCONE

被引：34

作者：

BAUMGARTNER, H ^{[1
]}

MARSCHNER, C ^{[1
]}

PUCHER, R ^{[1
]}

GRIENGL, H ^{[1
]}

机构：

[1] GRAZ UNIV TECHNOL,INST ORGAN CHEM,STREMAYRGASSE 16,A-8010 GRAZ,AUSTRIA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 05期

基金：

奥地利科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)74840-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By reaction of 1,2-anhydro-5-O-acetyl-3-O-benzyl-alpha-D-carbaxylofuranose 8 with the aglycone in alkaline medium followed by deprotection carbanucleosides 10 were obtained.

引用

页码：611 / 614

页数：4

共 23 条

[1] SYNTHESIS AND ANTIVIRAL ACTIVITY OF THE ENANTIOMERIC FORMS OF CARBA-5-IODO-2'-DEOXYURIDINE AND CARBA-(E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE [J].

BALZARINI, J ;

BAUMGARTNER, H ;

BODENTEICH, M ;

DECLERCQ, E ;

GRIENGL, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) :1861-1865

[2]

BAUMGARTNER H, 1988, TETRAHEDRON LETT, P5745

[3] SHORT CONVERGENT ROUTE TO HOMOCHIRAL CARBOCYCLIC 2'-DEOXYNUCLEOSIDES AND CARBOCYCLIC RIBONUCLEOSIDES [J].

BIGGADIKE, K ;

BORTHWICK, AD ;

EXALL, AM ;

KIRK, BE ;

ROBERTS, SM ;

YOUDS, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (14) :1083-1084

[4] SYNTHESIS AND ENZYMATIC RESOLUTION OF CARBOCYCLIC 2'-ARA-FLUORO-GUANOSINE - A POTENT NEW ANTI-HERPETIC AGENT [J].

BORTHWICK, AD ;

BUTT, S ;

BIGGADIKE, K ;

EXALL, AM ;

ROBERTS, SM ;

YOUDS, PM ;

KIRK, BE ;

BOOTH, BR ;

CAMERON, JM ;

COX, SW ;

MARR, CLP ;

SHILL, MD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) :656-658

[5] LARGE-SCALE PREPARATION OF (+)-ENDO-NORBORNENOL AND (-)-ENDO-NORBORNENOL BY ENZYMATIC-HYDROLYSIS [J].

EICHBERGER, G ;

PENN, G ;

FABER, K ;

GRIENGL, H .

TETRAHEDRON LETTERS, 1986, 27 (25) :2843-2844

[6] EFFICIENT STEREOCONTROLLED TOTAL SYNTHESES OF RACEMIC AND NATURAL BREFELDIN-A [J].

LEDRIAN, C ;

GREENE, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (20) :5473-5483

[7] SYNTHESIS AND ANTIVIRAL EVALUATION OF 6'-SUBSTITUTED ARISTEROMYCINS - POTENTIAL MECHANISM-BASED INHIBITORS OF S-ADENOSYLHOMOCYSTEINE HYDROLASE [J].

MADHAVAN, GVB ;

MCGEE, DPC ;

RYDZEWSKI, RM ;

BOEHME, R ;

MARTIN, JC ;

PRISBE, EJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) :1798-1804

[8] CARBOCYCLIC NUCLEOSIDES [J].

MARQUEZ, VE ;

LIM, MI .

MEDICINAL RESEARCH REVIEWS, 1986, 6 (01) :1-40

[9]

MARQUEZ VE, 1985, TETRAHEDRON LETT, P3669

[10] SYNTHESIS OF ALPHA-D-CARBARIBOFURANOSE AND BETA-D-CARBARIBOFURANOSE FROM (+)-NORBORN-5-EN-2-ONE [J].

MARSCHNER, C ;

PENN, G ;

GRIENGL, H .

TETRAHEDRON LETTERS, 1990, 31 (20) :2873-2874

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