A facile Er(OTf)3-catalyzed synthesis of 2,3-unsaturated O- and S-glycosides

被引：53
|
作者：
Procopio, Antonio
Dalpozzo, Renato
De Nino, Antonio
Maluolo, Loredana
Nardi, Monica
Oliverio, Manuela
Russo, Beatrice
机构：
[1] Univ Magna Gracia, Dipartimento Farmacobiol, I-88021 Roccelletta Di Borgia, CZ, Italy
[2] Univ Calabria, Dipartimento Chim, I-87030 Arcavacata Di Rende, CS, Italy
来源：
CARBOHYDRATE RESEARCH | 2007年 / 342卷 / 14期
关键词：
O-glycosylation; S-Glycosylation; lewis catalyst; erbium(III); triflate;
D O I：
10.1016/j.carres.2007.05.034
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Er(OTf3 is a useful catalyst for the Ferrier rearrangement furnishing high yields of O- and S-glycosides. The transforination has wide applicability, cleaner reaction profiles, mild reaction conditions, and high stereoselectivity and the catalyst, which is also commercially available, can be recovered and reused. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2125 / 2131
页数：7
相关论文
共 50 条
  • [1] 3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols
    Bodipati, Naganjaneyulu
    Palla, Srinivasa Rao
    Komera, Venkateshwarlu
    Peddinti, Rama Krishna
    TETRAHEDRON LETTERS, 2014, 55 (50) : 6878 - 6881
  • [2] FeCl3•6H2O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-Unsaturated O- and S-Glycosides
    Zhou, Jiafen
    Chen, Heshan
    Shan, Junjie
    Li, Juan
    Yang, Guofang
    Chen, Xuan
    Xin, Kunyun
    Zhang, Jianbo
    Tang, Jie
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2014, 33 (06) : 313 - 325
  • [3] Indium trichloride catalyzed Ferrier rearrangement - facile synthesis of 2,3-unsaturated glycosides
    Boga, SB
    Balasubramanian, KK
    ARKIVOC, 2004, : 87 - 102
  • [4] Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides
    Chen, Peiran
    Li, Shan
    TETRAHEDRON LETTERS, 2014, 55 (42) : 5813 - 5816
  • [5] Zn(OTf)2-Catalyzed Glycosylation of Glycals: Synthesis of 2,3-Unsaturated Glycosides via a Ferrier Reaction
    Narasimha, Gundeboina
    Srinivas, Batthula
    Krishna, Palakodety Radha
    Kashyap, Sudhir
    SYNLETT, 2014, 25 (04) : 523 - 526
  • [6] Progress in the Synthesis of 2,3-unsaturated Glycosides
    Jiang, Nan
    Wu, Zhengliang
    Dong, Youxian
    Xu, Xiaoxia
    Liu, Xiaxia
    Zhang, Jianbo
    CURRENT ORGANIC CHEMISTRY, 2020, 24 (02) : 184 - 199
  • [7] Ceric(IV) ammonium nitrate-catalyzed glycosidation of glycals: a facile synthesis of 2,3-unsaturated glycosides
    Yadav, JS
    Reddy, VBS
    Pandey, SK
    NEW JOURNAL OF CHEMISTRY, 2001, 25 (04) : 538 - 540
  • [8] Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides
    Tatina, Madhu Babu
    Xia Mengxin
    Rao Peilin
    Judeh, Zaher M. A.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 1275 - 1280
  • [9] Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement
    Chen, Peiran
    Su, Jie
    TETRAHEDRON, 2016, 72 (01) : 84 - 94
  • [10] Ruthenium catalyzed synthesis of 2,3-unsaturated C-glycosides from glycals
    Srinivas, Batthula
    Reddy, Thurpu Raghavender
    Kashyap, Sudhir
    CARBOHYDRATE RESEARCH, 2015, 406 : 86 - 92
12345