Synthesis of ethylene isosteres of β-D-galactosyl- and β-D-glucosyl-L-asparagine

被引:23
作者
Dondoni, A [1 ]
Massi, A [1 ]
Marra, A [1 ]
机构
[1] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy
关键词
amino acids and derivatives; carbohydrates; enol ethers; Mukaiyama reactions;
D O I
10.1016/S0040-4039(98)01376-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Mukaiyama-type coupling of galactosyl and glucosyl aldehydes with a four-carbon atom silyl enol ether carrying the oxazolidine ring affords the corresponding sugar containing aldols (65-74%) that upon deoxygenation and oxidative cleavage of the heterocyclic ring lead to the title carbon-linked beta-glycosyl amino acids. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6601 / 6604
页数:4
相关论文
共 24 条
  • [1] O-Glycosyl alpha-amino acids as building blocks for glycopeptide synthesis
    Arsequell, G
    Valencia, G
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (17) : 2839 - 2876
  • [2] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS
    BARTON, DHR
    MCCOMBIE, SW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16): : 1574 - 1585
  • [3] CARBON-LINKED GALACTOSPHINGOLIPID ANALOGS BIND SPECIFICALLY TO HIV-1 GP120
    BERTOZZI, CR
    COOK, DG
    KOBERTZ, WR
    GONZALEZSCARANO, F
    BEDNARSKI, MD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10639 - 10641
  • [4] Stereoselective synthesis of a C-glycosidic analog of N-glucoasparagine
    Burkhart, F
    Hoffmann, M
    Kessler, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (11): : 1191 - 1192
  • [5] TOTAL SYNTHESIS OF PROSTAGLANDINS . SYNTHESIS OF PURE DL-E1 -F1ALPHA -F1BETA -A1 AND -B1 HORMONES
    COREY, EJ
    ANDERSEN, NH
    CARLSON, RM
    PAUST, J
    VEDEJS, E
    VLATTAS, I
    WINTER, REK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (12) : 3245 - &
  • [6] Synthesis of carbon-linked glycopeptides through catalytic asymmetric hydrogenation
    Debenham, SD
    Debenham, JS
    Burk, MJ
    Toone, EJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (41) : 9897 - 9898
  • [7] REDUCTION OF ISOLATED OLEFINIC BONDS BY MEANS OF RHO-TOLUENESULFONYLHYDRAZINE
    DEWEY, RS
    VANTAMELEN, EE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (17) : 3729 - &
  • [8] Stereoselective synthesis of the C-linked analogue of β-D-galactopyranosyl-L-serine
    Dondoni, A
    Marra, A
    Massi, A
    [J]. TETRAHEDRON, 1998, 54 (12) : 2827 - 2832
  • [9] DONDONI A, 1998, IN PRESS CHEM COMMUN
  • [10] DONDONI A, 1994, J ORG CHEM, V59, P404