Glycosylation Reaction of Thioglycosides by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter

被引:11
|
作者
Kajimoto, Tetsuya [1 ]
Morimoto, Koji [1 ]
Ogawa, Ryosuke [2 ]
Dohi, Toshifumi [2 ]
Kita, Yasuyuki [1 ,2 ]
机构
[1] Ritsumeikan Univ, Res Org Sci & Technol, 1-1-1 Nojihigashi, Kusatsu, Shiga 5258577, Japan
[2] Ritsumeikan Univ, Coll Pharmaceut Sci, 1-1-1 Nojihigashi, Kusatsu, Shiga 5258577, Japan
基金
日本学术振兴会;
关键词
glycosylation; hypervalent iodine reagent; thioglycoside; ODORLESS BENZENETHIOLS; MEDIATED ACTIVATION; POLYVALENT IODINE; ORGANIC-SYNTHESIS; GLYCOSIDES; DONORS; CHEMISTRY; OLIGOSACCHARIDE; PRODUCT; LINKAGE;
D O I
10.1248/cpb.c16-00203
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Thioglycosides are available donors in glycosylation due to the stability of the anomeric C-S bond under general reaction conditions of protection and deprotection, and offer orthogonality in their activation. We report now that the hypervalent iodine effectively induced glycosylation reaction of thioglycosides with various alcohols. This method features a high efficiency, completion in a short time, and proceeding under very mild conditions.
引用
收藏
页码:838 / 844
页数:7
相关论文
共 50 条
  • [41] Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
    Deruer, Elsa
    Hamel, Vincent
    Blais, Samuel
    Canesi, Sylvain
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 1203 - 1207
  • [42] Environmentally benign synthesis of isoflavone derivatives using polymer-supported hypervalent iodine(III) reagent
    Kawamura, Y
    Maruyama, M
    Yamashita, K
    Tsukayama, M
    INTERNATIONAL JOURNAL OF MODERN PHYSICS B, 2003, 17 (8-9): : 1482 - 1486
  • [43] DECARBOXYLATIVE HALOGENATION OF INDOLECARBOXYLIC ACIDS USING HYPERVALENT IODINE(III) REAGENT AND ITS APPLICATION TO THE SYNTHESIS OF POLYBROMOINDOLES
    Hamamoto, Hiromi
    Umemoto, Hideaki
    Umemoto, Misako
    Ohta, Chiaki
    Fujita, Emi
    Nakamura, Akira
    Maegawa, Tomohiro
    Miki, Yasuyoshi
    HETEROCYCLES, 2015, 91 (03) : 561 - 572
  • [44] A Simple and Efficient Method for the Synthesis of Novel Pyrazolyl Isoxazoline Derivatives Using Hypervalent Iodine (III) Reagent
    Kumar, Rajesh
    Kumar, Manoj
    Prakash, Om
    HETEROATOM CHEMISTRY, 2016, 27 (04) : 228 - 234
  • [45] An unexpected intermolecular chiral biaryl coupling reaction induced by a hypervalent iodine(III) reagent: synthesis of potential precursor for ellagitannin
    Arisawa, M
    Utsumi, S
    Nakajima, M
    Ramesh, NG
    Tohma, H
    Kita, Y
    CHEMICAL COMMUNICATIONS, 1999, (05) : 469 - 470
  • [46] New achievements in the field of intramolecular phenolic coupling reactions, using hypervalent (III) iodine reagent: Synthesis of galanthamine
    Krikorian, D
    Tarpanov, V
    Parushev, S
    Mechkarova, P
    SYNTHETIC COMMUNICATIONS, 2000, 30 (16) : 2833 - 2846
  • [47] A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent
    Qiu, Li-Jun
    Liu, Dan
    Zheng, Ke
    Zhang, Ming-Tao
    Zhang, Chi
    FRONTIERS IN CHEMISTRY, 2020, 8
  • [48] An Efficient and Regioselective Monobromination of Electron-Rich Aromatic Compounds Using Catalytic Hypervalent Iodine(III) Reagent
    Zhou, Zhongshi
    He, Xuehan
    SYNTHESIS-STUTTGART, 2011, (02): : 207 - 209
  • [49] Synthesis of α-Azido Ketones and Esters Using Recyclable Hypervalent Iodine Reagent
    Telvekar, Vikas N.
    Patile, Hemlata V.
    SYNTHETIC COMMUNICATIONS, 2011, 41 (01) : 131 - 135
  • [50] Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride
    Geary, Gemma C.
    Hope, Eric G.
    Singh, Kuldip
    Stuart, Alison M.
    CHEMICAL COMMUNICATIONS, 2013, 49 (81) : 9263 - 9265