One-pot synthesis of β-2,6-dideoxyglycosides via glycosyl iodide intermediates

被引：8
|
作者：
Zhang, Wan [1 ]
Luo, Xiaosheng [1 ]
Wang, Zhongfu [2 ]
Zhang, Jianbo [1 ]
机构：
[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai 200241, Peoples R China
[2] Northwestern Univ, Sch Life Sci, Xian, Peoples R China
来源：
JOURNAL OF CARBOHYDRATE CHEMISTRY | 2016年 / 35卷 / 06期
基金：
上海市自然科学基金;
关键词：
2,6-dideoxy oligosaccharide; beta-2,6-dideoxyglycoside; glycosyl iodide intermediate; one-pot synthesis; STEREOSELECTIVE-SYNTHESIS; 2-DEOXY-BETA-GLYCOSIDES; DIGITOXIN; 2-DEOXY; BIOSYNTHESIS; ACTIVATION; CHEMISTRY; EFFICIENT; FAMILY; SCOPE;
D O I：
10.1080/07328303.2016.1239729
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：
An efficient and convenient approach for stereoselective synthesis of beta-linked 2,6-dideoxyglycosides has been developed through one-pot glycosylation strategy using glycosyl iodide intermediates. The glycosidation reaction, promoted by easily available silver nitrate, provided the corresponding 2,6-dideoxyglycosides and oligosaccharides with preponderant beta-configuration (beta/alpha = 2.3:1 to 11:1) and good to excellent yields (52-84%).
引用
收藏
页码：315 / 325
页数：11
相关论文
共 50 条
  • [1] Synthesis of 2,6-dideoxyglycosides by conjugate addition.
    Koviach, JL
    Domush, HL
    Mann, BE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U311 - U311
  • [2] One-pot conversion reactions of glycosyl boranophosphates into glycosyl phosphate derivatives via acyl phosphite intermediates
    Sato, Kazuki
    Wada, Takeshi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (47) : 11092 - 11095
  • [3] Merging total synthesis and NMR technology for deciphering the realistic structure of natural 2,6-dideoxyglycosides
    Zhang, Zhaolun
    Wu, Renjie
    Cao, Shen
    Li, Jiaji
    Huang, Guangen
    Wang, Haoyu
    Yang, Tao
    Tang, Wei
    Xu, Peng
    Yu, Biao
    SCIENCE ADVANCES, 2024, 10 (15):
  • [4] Efficient one-pot synthesis of glycosyl disulfides
    Morais, Goreti Ribeiro
    Falconer, Robert A.
    TETRAHEDRON LETTERS, 2007, 48 (43) : 7637 - 7641
  • [5] Scope and Limitations of 2-Deoxy- and 2,6-Dideoxyglycosyl Bromides as Donors for the Synthesis of β-2-Deoxy- and β-2,6-Dideoxyglycosides
    Kaneko, Miho
    Herzon, Seth B.
    ORGANIC LETTERS, 2014, 16 (10) : 2776 - 2779
  • [6] A ONE-POT SYNTHESIS OF CONJUGATED FLUOROENYNES VIA 2,2-DIFLUOROVINYLCOPPER INTERMEDIATES
    ICHIKAWA, J
    IKEURA, C
    MINAMI, T
    JOURNAL OF FLUORINE CHEMISTRY, 1993, 63 (03) : 281 - 285
  • [7] One-pot synthesis of glycosyl phenylthiosulfonates from sulfinate, S and glycosyl bromides
    Feng, Chunlai
    Wang, Jin
    Tang, Qiujie
    Zhong, Zijian
    Qiao, Shusen
    Liu, Xingyu
    Chen, Can
    Zhou, Aihua
    CARBOHYDRATE RESEARCH, 2019, 471 : 1 - 5
  • [8] Preparation of glycosyl thiourea derivatives from glycosyl azides using sulfamic acid and sodium iodide in one-pot
    Gucchait, Arin
    Jana, Manas
    Jana, Kuladip
    Misra, Anup Kumar
    CARBOHYDRATE RESEARCH, 2016, 434 : 107 - 112
  • [9] ONE-POT STEREOSELECTIVE SYNTHESIS OF GLYCOSYL AZIDES VIA 1,2-CYCLIC SULFITE
    ELMESLOUTI, A
    BEAUPERE, D
    DEMAILLY, G
    UZAN, R
    TETRAHEDRON LETTERS, 1994, 35 (23) : 3913 - 3916
  • [10] Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis
    Pornsuriyasak, P
    Demchenko, AV
    TETRAHEDRON-ASYMMETRY, 2005, 16 (02) : 433 - 439
12345