A study of polymer-supported bases for the solution phase synthesis of glycosyl trichloroacetimidates

被引:19
|
作者
Chiara, JL [1 ]
Encinas, L [1 ]
Díaz, B [1 ]
机构
[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
关键词
carbohydrates; solid-supported reagents; glycosylation;
D O I
10.1016/j.tetlet.2005.02.055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polystyrene-supported strong organic bases are highly efficient reagents for the solution-phase synthesis of glycosyl trichloroacetimidates, affording quantitative yields of pure products in short reaction times after simple filtration and evaporation. Although efficiency of the different bases varies with substrate structure, polymer-bound 1,8-diazabicyclo[5.4.0]undec-7-ene was found to give the best results for all the substrates tested. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2445 / 2448
页数:4
相关论文
共 50 条
  • [1] Polymer-supported syntheses of oligosaccharides: Using dibutylboron triflate to promote glycosylations with glycosyl trichloroacetimidates.
    Wang, ZG
    Douglas, SP
    Krepinsky, JJ
    TETRAHEDRON LETTERS, 1996, 37 (39) : 6985 - 6988
  • [2] Polymer-supported solution phase synthesis of oligosaccharides.
    Krepinsky, JJG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U168 - U168
  • [3] Synthesis of a polymer-supported sialic acid glycosyl donor
    Kononov, LO
    Ito, Y
    Ogawa, T
    TETRAHEDRON LETTERS, 1997, 38 (09) : 1599 - 1602
  • [4] POLYMER-SUPPORTED BASES .3. SYNTHESIS OF PHOSPHATIDYLCHOLINES USING POLYMER-SUPPORTED AMINOPYRIDINES
    TOMOI, M
    GOTO, M
    KAKIUCHI, H
    NOGUCHI, Y
    MAKROMOLEKULARE CHEMIE-RAPID COMMUNICATIONS, 1985, 6 (06): : 397 - 401
  • [5] POLYMER-SUPPORTED SOLUTION SYNTHESIS OF OLIGOSACCHARIDES
    KREPINSKY, JJ
    DOUGLAS, SP
    WHITFIELD, DM
    NEOGLYCOCONJUGATES, PT A, 1994, 242 : 280 - 293
  • [6] POLYMER-SUPPORTED SOLUTION SYNTHESIS OF OLIGOSACCHARIDES
    DOUGLAS, SP
    WHITFIELD, DM
    KREPINSKY, JJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) : 5095 - 5097
  • [7] POLYMER-SUPPORTED SOLUTION SYNTHESIS OF OLIGOSACCHARIDES
    KREPINSKY, JJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 30 - BTEC
  • [8] POLYMER-SUPPORTED BASES .10. SYNTHESIS OF PHOSPHATIDYLCHOLINES USING POLYMER-SUPPORTED OR FREE ACYLIMIDAZOLES
    TOMOI, M
    INOMATA, K
    KAKIUCHI, H
    SYNTHETIC COMMUNICATIONS, 1989, 19 (5-6) : 907 - 915
  • [9] Polymer-supported Lewis acids and bases: Synthesis and applications
    Yolsal, Utku
    Horton, Thomas A. R.
    Wang, Meng
    Shaver, Michael P.
    PROGRESS IN POLYMER SCIENCE, 2020, 111
  • [10] POLYMER-SUPPORTED BASES .12. REGIOSELECTIVE SYNTHESIS OF LYSOPHOSPHOLIPIDS USING POLYMER-SUPPORTED BICYCLIC AMIDINES OR GUANIDINES
    TAMURA, Y
    FUKUDA, W
    TOMOI, M
    TOKUYAMA, S
    SYNTHETIC COMMUNICATIONS, 1994, 24 (20) : 2907 - 2914