GLYCOSYLIDENE CARBENES .9. FULLERENE SUGARS - PREPARATION OF ENANTIOMERICALLY PURE, SPIRO-LINKED C-GLYCOSIDES OF C-60

被引:187
作者
VASELLA, A [1 ]
UHLMANN, P [1 ]
WALDRAFF, CAA [1 ]
DIEDERICH, F [1 ]
THILGEN, C [1 ]
机构
[1] SWISS FED INST TECHNOL,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 10期
关键词
D O I
10.1002/anie.199213881
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sweetened buckyballs are prepared in good yields. The C-glycosylated, uniform, enantiomerically pure C60 mono-addition products 1 (R = benzyl, pivaloyl) are differentiated not only by their chiroptical properties, but also by the conformation of the glycosyl residue, which is dependent on its substituents.
引用
收藏
页码:1388 / 1390
页数:3
相关论文
共 24 条
  • [1] (ETA-2-C70)IR(CO)CL(PPH3)2 - THE SYNTHESIS AND STRUCTURE OF AN ORGANOMETALLIC DERIVATIVE OF A HIGHER FULLERENE
    BALCH, AL
    CATALANO, VJ
    LEE, JW
    OLMSTEAD, MM
    PARKIN, SR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) : 8953 - 8955
  • [2] ACCUMULATING EVIDENCE FOR THE SELECTIVE REACTIVITY OF THE 6-6 RING FUSION OF C-60 - PREPARATION AND STRUCTURE OF (ETA-2-C60)IR(CO)CL(PPH3)2.5C6H6
    BALCH, AL
    CATALANO, VJ
    LEE, JW
    [J]. INORGANIC CHEMISTRY, 1991, 30 (21) : 3980 - 3981
  • [3] CONSIDERED NOVEL AROMATIC SYSTEMS .11. DIAMAGNETIC POLYANIONS OF THE C60 AND C70 FULLERENES - PREPARATION, C-13 AND LI-7 NMR SPECTROSCOPIC OBSERVATION, AND ALKYLATION WITH METHYL-IODIDE TO POLYMETHYLATED FULLERENES
    BAUSCH, JW
    PRAKASH, GKS
    OLAH, GA
    TSE, DS
    LORENTS, DC
    BAE, YK
    MALHOTRA, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) : 3205 - 3206
  • [4] PREPARATION AND CHARACTERIZATION OF C60BR6 AND C60BR8
    BIRKETT, PR
    HITCHCOCK, PB
    KROTO, HW
    TAYLOR, R
    WALTON, DRM
    [J]. NATURE, 1992, 357 (6378) : 479 - 481
  • [5] GLYCOSYLIDENE CARBENES .2. SYNTHESIS OF O-ARYL GLYCOSIDES
    BRINER, K
    VASELLA, A
    [J]. HELVETICA CHIMICA ACTA, 1990, 73 (06) : 1764 - 1778
  • [6] GLYCOSYLIDENE CARBENES - A NEW APPROACH TO GLYCOSIDE SYNTHESIS .1. PREPARATION OF GLYCOSYLIDENE-DERIVED DIAZIRIDINES AND DIAZIRINES
    BRINER, K
    VASELLA, A
    [J]. HELVETICA CHIMICA ACTA, 1989, 72 (06) : 1371 - 1382
  • [7] SYNTHESIS AND CHARACTERIZATION OF (C60)O, THE 1ST FULLERENE EPOXIDE
    CREEGAN, KM
    ROBBINS, JL
    ROBBINS, WK
    MILLAR, JM
    SHERWOOD, RD
    TINDALL, PJ
    COX, DM
    SMITH, AB
    MCCAULEY, JP
    JONES, DR
    GALLAGHER, RT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) : 1103 - 1105
  • [8] THE HIGHER FULLERENES - ISOLATION AND CHARACTERIZATION OF C76, C84, C90, C94, AND C70O, AN OXIDE OF D5H-C70
    DIEDERICH, F
    ETTL, R
    RUBIN, Y
    WHETTEN, RL
    BECK, R
    ALVAREZ, M
    ANZ, S
    SENSHARMA, D
    WUDL, F
    KHEMANI, KC
    KOCH, A
    [J]. SCIENCE, 1991, 252 (5005) : 548 - 551
  • [9] REACTION OF C-60 WITH DIMETHYLDIOXIRANE - FORMATION OF AN EPOXIDE AND A 1,3-DIOXOLANE DERIVATIVE
    ELEMES, Y
    SILVERMAN, SK
    SHEU, CM
    KAO, M
    FOOTE, CS
    ALVAREZ, MM
    WHETTEN, RL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (03): : 351 - 353
  • [10] ELEMES Y, 1992, ANGEW CHEM, V104, P364