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
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
收藏
页码:611 / 614
页数:4
相关论文
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
    BALZARINI, J
    BAUMGARTNER, H
    BODENTEICH, M
    DECLERCQ, E
    GRIENGL, H
    [J]. 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
    BIGGADIKE, K
    BORTHWICK, AD
    EXALL, AM
    KIRK, BE
    ROBERTS, SM
    YOUDS, P
    [J]. 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
    BORTHWICK, AD
    BUTT, S
    BIGGADIKE, K
    EXALL, AM
    ROBERTS, SM
    YOUDS, PM
    KIRK, BE
    BOOTH, BR
    CAMERON, JM
    COX, SW
    MARR, CLP
    SHILL, MD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) : 656 - 658
  • [5] LARGE-SCALE PREPARATION OF (+)-ENDO-NORBORNENOL AND (-)-ENDO-NORBORNENOL BY ENZYMATIC-HYDROLYSIS
    EICHBERGER, G
    PENN, G
    FABER, K
    GRIENGL, H
    [J]. TETRAHEDRON LETTERS, 1986, 27 (25) : 2843 - 2844
  • [6] EFFICIENT STEREOCONTROLLED TOTAL SYNTHESES OF RACEMIC AND NATURAL BREFELDIN-A
    LEDRIAN, C
    GREENE, AE
    [J]. 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
    MADHAVAN, GVB
    MCGEE, DPC
    RYDZEWSKI, RM
    BOEHME, R
    MARTIN, JC
    PRISBE, EJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) : 1798 - 1804
  • [8] CARBOCYCLIC NUCLEOSIDES
    MARQUEZ, VE
    LIM, MI
    [J]. 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
    MARSCHNER, C
    PENN, G
    GRIENGL, H
    [J]. TETRAHEDRON LETTERS, 1990, 31 (20) : 2873 - 2874