A convenient synthesis of iminosugar-C-glycosides via organometallic addition to N-benzyl-N-glycosylhydroxylamines

被引：46
|
作者：
Dondoni, A [1 ]
Perrone, D [1 ]
机构：
[1] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy
来源：
TETRAHEDRON | 2003年 / 59卷 / 24期
关键词：
nitrones; N-benzyl-N-glycosylhydroxylamines; iminosugars; glycosidase inhibitors; organometallic addition;
D O I：
10.1016/S0040-4020(03)00631-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Benzyl-N-glycosylhydroxylamines were prepared in very good yield via condensation of furanoses and pyranoses with N-benzylhydroxylamine at 110degreesC for 30 min under solvent-free conditions. These anomeric sugar-hydroxylamines exist in equilibrium with the open-chain nitrone form. In fact upon treatment with various organometallic reagents, the corresponding adducts were obtained with good to high diastereoselectivity. These adducts were converted into iminosugar-C-glycosides by reductive dehydroxylation and intramolecular cyclization. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
下载
收藏
页码：4261 / 4273
页数：13
相关论文
共 50 条
  • [1] Stereoselective Synthesis of Iminosugar-C-Glycosides through Addition of Organometallic Reagents to N-tert-Butanesulfinyl Glycosylamines: A Comprehensive Study
    Kamzol, Daniel
    Neuville, Maxime
    Cocaud, Chloe
    Tiger, Killian
    Taffoureau, Baptiste
    Lewinski, Krzysztof
    Jaszczyk, Justyna
    Martin, Olivier R.
    Bas, Sebastian
    Routier, Sylvain
    Gillaizeau, Isabelle
    Buron, Frederic
    Nicolas, Cyril
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (39)
  • [2] Synthesis of N-Substituted Iminosugar C-Glycosides and Evaluation as Promising α-Glucosidase Inhibitors
    Wang, Haibo
    Tang, Senling
    Zhang, Guoqing
    Pan, Yang
    Jiao, Wei
    Shao, Huawu
    MOLECULES, 2022, 27 (17):
  • [3] CONVENIENT SYNTHESIS OF N-BENZYL-N'-ACYL-PIPERAZINES
    GARDINI, GP
    PALLA, G
    SCAPINI, G
    CESARONI, MR
    SYNTHETIC COMMUNICATIONS, 1982, 12 (11) : 887 - 890
  • [4] A CONVENIENT SYNTHESIS OF N-ARYL-N'-BENZYL-1,2-ETHANEDIAMINES
    LIS, R
    MARISCA, AJ
    SYNTHETIC COMMUNICATIONS, 1988, 18 (01) : 45 - 50
  • [5] NUCLEOSIDE SYNTHESIS VIA N-PENTENYL GLYCOSIDES
    CHAPEAU, MC
    MARNETT, LJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 74 - ORGN
  • [6] CONVENIENT KETONE SYNTHESIS VIA N-ACYLAZIRIDINES
    WATTANASIN, S
    KATHAWALA, FG
    TETRAHEDRON LETTERS, 1984, 25 (08) : 811 - 814
  • [7] A convenient synthesis of (S)-O-benzyl-N-tert-butoxycarbonyl-β-tyrosine
    Andruszkiewicz, R
    Treder, A
    POLISH JOURNAL OF CHEMISTRY, 2004, 78 (08) : 1081 - 1084
  • [8] Synthesis of α- and β-C-glycosides of N-acetylglucosamine
    McGarvey, GJ
    Schmidtmann, FW
    Benedum, TE
    Kizer, DE
    TETRAHEDRON LETTERS, 2003, 44 (19) : 3775 - 3779
  • [9] CONVENIENT SYNTHESIS OF 6-N-METHYLPURPUROSAMINE-C
    OHASHI, Y
    OKUNO, S
    TAKEDA, K
    ITO, Y
    CARBOHYDRATE RESEARCH, 1978, 67 (02) : 503 - 508
  • [10] Application of polymer supported base in solid phase synthesis:: Convenient synthesis of N-aryl-N′-benzyl piperazine derivatives
    Yamamoto, Y
    Tanabe, K
    Okonogi, T
    CHEMISTRY LETTERS, 1999, (02) : 103 - 104
12345