Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2-O-iso-propylidene-α-D-xylo-hex-enofuranose

被引:0
|
作者
Al-Timari, U.A.R. [1 ]
Fisera, L. [1 ]
机构
[1] Department of Organic Chemistry, Slovak Technical University, CS-81237 Bratislava, Czechoslovakia
关键词
Drug Products - Antibiotics - Organic Compounds - Physical Properties - Sugars - Addition Reactions;
D O I
10.1016/0008-6215(91)84091-R
中图分类号
学科分类号
摘要
The synthesis of 3-aryl-5-(1,2-O-isopropylidene-α- D-xylo-tetrofuranos-4-yl) -2-isoxazoline (3) from arylnitrile oxides and 5,6-dideoxy-1,2-O-isopropyl- idene-α-D-xylo-hex-5-enofuranose (1) is described. The 1,3-dipolar cycloaddition reactions give mainly anti-adducts (≥ 95% π-facial stereoselectivity).
引用
收藏
页码:121 / 127
相关论文
共 12 条
  • [1] REGIOSELECTIVE SYNTHESIS OF C-NUCLEOSIDES BY 1,3-DIPOLAR CYCLOADDITION OF ARYLNITRILE OXIDES TO 5,6-DIDEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-HEX-5-ENOFURANOSE
    ALTIMARI, UAR
    FISERA, L
    CARBOHYDRATE RESEARCH, 1991, 218 : 121 - 127
  • [2] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF CARBOHYDRATE ISOXAZOLIDINES BY 1,3-DIPOLAR CYCLOADDITION OF NITRONES TO 5,6-DIDEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-HEX-5-ENOFURANOSE
    ALTIMARI, UAR
    FISERA, L
    GOLJER, I
    ERTL, P
    CARBOHYDRATE RESEARCH, 1992, 226 (01) : 49 - 56
  • [3] HYDROFORMYLATION OF 5,6-DIDEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-HEX-5-ENOFURANOSE
    ROSENTHAL, A
    KAN, G
    JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (04): : 592 - +
  • [4] 1,3-dipolar cycloaddition on ethyl 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate
    Jedlovska, E
    Sapik, M
    Fisera, L
    CHEMICAL PAPERS, 1997, 51 (6B) : 427 - 431
  • [5] CYCLOADDITION OF NITRILE OXIDES TO 3-O-BENZYL-5,6-DIDEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-RIBO-HEX-5-ENOFURANOSE
    BLAKE, AJ
    GOULD, RO
    MCGHIE, KE
    PATON, RM
    REED, D
    SADLER, IH
    YOUNG, AA
    CARBOHYDRATE RESEARCH, 1991, 216 : 461 - 473
  • [6] BRANCHED-CHAIN SUGARS .3. ADDITION OF VINYLMAGNESIUM BROMIDE TO 5,6-DIDEOXY-1,2-O-ISOPROPYLIDENE-6-C-NITRO-3-O-SUBSTITUTED-ALPHA-D-XYLO-HEX-5-ENOFURANOSES
    IIDA, T
    FUNABASH.M
    YOSHIMUR.J
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (10) : 3203 - 3206
  • [7] 1,3-dipolar cycloaddition of 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose and C60
    Marco-Contelles, J
    Jagerovic, N
    Alhambra, C
    JOURNAL OF CHEMICAL RESEARCH-S, 1999, (11): : 680 - 681
  • [8] Cycloaddition of cyclopentadiene to 3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-erythro-hex-3-enofuranose. Synthesis and representative chemistry of 1,6-anhydro-2,3-dideoxy-beta-D-glycero-hex-2-enopyran-4-ulose (''isolevoglucosenone'')
    Horton, D
    Roski, JP
    Norris, P
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11): : 3783 - 3793
  • [9] 1ST X-RAY STUDY ON ORIENTATION OF ADDITION OF PHOSPHORUS-COMPOUNDS TO 3-O-ALKYL-5,6-DIDEOXY-1,2-O-ISOPROPYLIDENE-6-C-NITRO-ALPHA-D-XYLO-HEXO-5-(Z)-ENOFURANOSES
    YAMASHITA, M
    SUGIURA, M
    TAMADA, Y
    OSHIKAWA, T
    CLARDY, J
    CHEMISTRY LETTERS, 1987, (07) : 1407 - 1408
  • [10] STEREOSELECTIVE SYNTHESIS OF NITROPYRAZOLINES - 1,3-DIPOLAR CYCLOADDITION OF DIAZOALKANES TO (E)-4,5,6,7,8-PENTA-O-ACETYL-1,2,3-TRIDEOXY-2-C-NITRO-D-MANNO-OCT-2-ENITOL
    MANCERA, M
    RODRIGUEZ, E
    ROFFE, I
    GALBIS, JA
    CONDE, CF
    CONDE, A
    CARBOHYDRATE RESEARCH, 1991, 210 : 327 - 332