A stereoselective synthesis of methyl β-C-lactoside through the tether approach

被引:30
作者
Rubinstenn, G [1 ]
Mallet, JM [1 ]
Sinaÿ, P [1 ]
机构
[1] Ecole Normale Super, CNRS, Dept Chim, F-75231 Paris 05, France
关键词
D O I
10.1016/S0040-4039(98)00649-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyl beta-C-lactoside (beta-D-Galp-C-(1-->4)-beta-Glcp-OMe) is stereoselectively synthesized by radical coupling of phenyl Se-beta-D-galactopyranoside 5 onto exo-methylene-sugar 4, which are temporarily connected through a silaketal tether. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3697 / 3700
页数:4
相关论文
共 31 条
  • [1] APPLICATIONS OF RADICAL-ADDITION REACTIONS TO THE SYNTHESIS OF A C-GLUCOSIDE AND A FUNCTIONALIZED AMINO-ACID
    ADLINGTON, RM
    BALDWIN, JE
    BASAK, A
    KOZYROD, RP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) : 944 - 945
  • [2] STRATEGIES FOR THE SYNTHESIS OF C-DISACCHARIDES CONTAINING D-SUGAR AND L-SUGAR
    ARMSTRONG, RW
    SUTHERLIN, DP
    [J]. TETRAHEDRON LETTERS, 1994, 35 (42) : 7743 - 7746
  • [3] Berthault P, 1996, J BIOMOL NMR, V8, P23
  • [4] SILICON-TETHERED REACTIONS
    BOLS, M
    SKRYDSTRUP, T
    [J]. CHEMICAL REVIEWS, 1995, 95 (05) : 1253 - 1277
  • [5] AN IMPROVED PREPARATION OF 3,4-O-ISOPROPYLIDENE DERIVATIVES OF ALPHA-D-GALACTOPYRANOSIDES AND BETA-D-GALACTOPYRANOSIDES
    CATELANI, G
    COLONNA, F
    MARRA, A
    [J]. CARBOHYDRATE RESEARCH, 1988, 182 (02) : 297 - 300
  • [6] CHENEDE A, 1994, SYNLETT, P420
  • [7] DIETRICH H, 1994, LIEBIGS ANN CHEM, P975
  • [8] Conformational differences of O- and C-glycosides in the protein-bound state: Different conformations of C-lactose and its O-analogue are recognized by ricin B, a galactose-binding protein
    Espinosa, JF
    Canada, FJ
    Asensio, JL
    Dietrich, H
    MartinLomas, M
    Schmidt, RR
    JimenezBarbero, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (03): : 303 - 306
  • [9] EXPERIMENTAL AND THEORETICAL EVIDENCES OF CONFORMATIONAL FLEXIBILITY OF C-GLYCOSIDES - NMR ANALYSIS AND MOLECULAR MECHANICS CALCULATIONS OF C-LACTOSE AND ITS O-ANALOG
    ESPINOSA, JF
    MARTINPASTOR, M
    ASENSIO, JL
    DIETRICH, H
    MARTINLOMAS, M
    SCHMIDT, RR
    JIMENEZBARBERO, J
    [J]. TETRAHEDRON LETTERS, 1995, 36 (35) : 6329 - 6332
  • [10] Escherichia coli β-galactosidase recognizes a high-energy conformation of C-lactose, a nonhydrolizable substrate analogue.: NMR and modeling studies of the molecular complex
    Espinosa, JF
    Montero, E
    Vian, A
    García, JL
    Dietrich, H
    Schmidt, RR
    Martín-Lomas, M
    Imberty, A
    Cañada, FJ
    Jiménez-Barbero, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (06) : 1309 - 1318