Facile synthesis of fused furanosyl β-amino acids from protected sugar lactones:: incorporation into a peptide chain

被引：25
|
作者：
Taillefumier, C
Lakhrissi, Y
Lakhrissi, M
Chapleur, Y
机构：
[1] Univ Nancy 1, CNRS, UMR 7565, Grp SUCRES, F-54506 Vandoeuvre Les Nancy, France
[2] Univ Ibn Tofail, Fac Sci, Lab Synthese Organ, Kenitra, Morocco
来源：
TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 16期
关键词：
D O I：
10.1016/S0957-4166(02)00473-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis of fused furanosyl beta-amino esters from protected sugar lactones is described, using the combination of a Wittig type reaction and 1,4-addition of benzylamine on the resulting glycosylidenes. This sequence of reactions afford either N-glycosyl-3-ulosonic acid esters, which are the beta-analogues of anomeric sugar alpha-amino esters, or open-chain sugar beta-enamino esters, when a retro-Michael reaction takes place after addition of benzylamine. Incorporation of the fused furanosyl beta-amino ester 2a into a peptide chain is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1707 / 1711
页数：5
相关论文
共 50 条
  • [1] Synthesis of conformationally rigid sugar-fused lactones and sugar α-amino acids
    Gupta, Shilpi
    Bera, Smritilekha
    Mondal, Dhananjoy
    TETRAHEDRON, 2023, 146
  • [2] Facile Synthesis of N α -Protected Amino/Peptide Hydroxamic Acids Mediated by COMU
    Panguluri, Nageswara Rao
    Basavaprabhu
    Sureshbabu, Vommina V.
    INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2014, 20 (03) : 377 - 384
  • [3] Facile Synthesis of Nα-Protected Amino/Peptide Hydroxamic Acids Mediated by COMU
    Nageswara Rao Panguluri
    Vommina V. Basavaprabhu
    International Journal of Peptide Research and Therapeutics, 2014, 20 : 377 - 384
  • [4] Facile synthesis of protected hydrazino amino acids
    Oguz, U
    McLaughlin, ML
    BIOPOLYMERS, 2003, 71 (03) : 345 - 345
  • [5] Facile synthesis of protected hydrazino amino acids
    Oguz, Umut
    McLaughlin, Mark L.
    PEPTIDE REVOLUTION: GENOMICS, PROTEOMICS & THERAPEUTICS, 2004, : 83 - 84
  • [6] Synthesis of orthogonally protected cyclic homooligomers from sugar amino acids
    Ménand, M
    Blais, JC
    Hamon, L
    Valéry, JM
    Xie, J
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11): : 4423 - 4430
  • [7] A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids
    M. Arfan
    A. Tahira
    A. Mannan
    T. Fatima
    Russian Journal of Organic Chemistry, 2020, 56 : 292 - 297
  • [8] A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids
    Arfan, M.
    Tahira, A.
    Mannan, A.
    Fatima, T.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (02) : 292 - 297
  • [9] Facile synthesis of sterically hindered α,α-disubstituted amino acids and their incorporation into peptides by solid phase peptide synthesis.
    Fu, YW
    Miller, TJ
    Hammarstrom, LGJ
    McLaughlin, ML
    Hammer, RP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U46 - U46
  • [10] Inverse Peptide Synthesis Using Transient Protected Amino Acids
    Liu, Tao
    Peng, Zejun
    Lai, Manting
    Hu, Long
    Zhao, Junfeng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (06) : 4270 - 4280
12345