A novel method for solid-phase synthesis of oligosaccharides using the N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde) linker

被引：8
|
作者：
Drinnan, N
West, ML
Broadhurst, M
Kellam, B
Toth, I
机构：
[1] Alchemia Pty Ltd, Eight Mile Plains, Qld 4113, Australia
[2] Univ London, Sch Pharm, London WC1N 1AX, England
[3] Univ Queensland, Sch Pharm, Brisbane, Qld 4072, Australia
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 06期
关键词：
solid-phase/oligosaccharide synthesis; dimedone based linker;
D O I：
10.1016/S0040-4039(00)02197-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The application of the N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde) linker for the solid-phase synthesis of oligosaccharides is described. The oligosaccharide products can be cleaved from the resin by hydrazine, ammonia or primary amines, but the linker is stable under the conditions of oligosaccharide synthesis. The first sugar can be attached to the resin linker via a vinylogous amide bond, or by ether linkage using a p-aminobenzyl alcohol converter. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1159 / 1162
页数：4
相关论文
共 24 条
  • [1] N-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl (N-Dde) Lipoamino Acids
    Ross, Benjamin P.
    Falconer, Robert A.
    Toth, Istvan
    MOLBANK, 2008, (02)
  • [2] POLYMERS WITH ENAMINOKETONE GROUPS .1. SYNTHESIS AND CHARACTERIZATION OF POLYSTYRENES WITH (4,4-DIMETHYL-2,6-DIOXOCYCLOHEXYLIDENE)-2-METHYLAMINOPHENYL-THIO ENDGROUPS
    TRATHNIGG, B
    HEITZ, W
    ANGEWANDTE MAKROMOLEKULARE CHEMIE, 1979, 81 (SEP): : 171 - 178
  • [3] Synthesis, antimicrobial activity and docking study of some novel 4-(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino derivatives carrying biologically active sulfonamide moiety
    Ghorab, Mostafa M.
    Soliman, Aiten M.
    Alsaid, Mansour S.
    Askar, Ahmed A.
    ARABIAN JOURNAL OF CHEMISTRY, 2020, 13 (01) : 545 - 556
  • [4] Synthesis and application of N-[1-(4-(4-fluorophenyl)-2,6-dioxocyclohexylidene)ethyl] (Fde)-protected amino acids for optimization of solid-phase peptide synthesis using gel-phase 19F NMR spectroscopy
    Pudelko, Maciej
    Qian, Weixing
    Elofsson, Mikael
    JOURNAL OF PEPTIDE SCIENCE, 2009, 15 (04) : 264 - 271
  • [5] Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene) methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S •C2H4O2
    Ghorab, Mostafa M.
    Alsaid, Mansour S.
    Al-Dosari, Mohmmed S.
    Ghabbour, Hazem A.
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2017, 232 (03): : 417 - 419
  • [6] The synthesis of 3-acetyl-2-(4,4-dimethyl-2,6-dioxocyclohexyl)-1-phenylpentanedione-1,4 and its reactions with N-nucleophiles
    Andin, AN
    Kaminskii, VA
    Dubovitskii, SV
    HETEROCYCLIC COMMUNICATIONS, 2001, 7 (02) : 155 - 158
  • [7] Solid-phase synthesis of rigid acylpolyamines using temporary N-4,4′-dimethoxytrityl protection in the presence of trityl linkers
    Olsen, CA
    Witt, M
    Jaroszewski, JW
    Franzyk, H
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18): : 6149 - 6152
  • [8] A facile solid-phase synthesis of 1,2,4,5-tetrasubstituted imidazoles using sodium benzenesulfinate as a traceless linker
    Li, WW
    Lam, YL
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (05): : 644 - 647
  • [9] Solid-phase synthesis of 4-amino spiro [benzopyran-2,4'-n-methylpiperidines] using a nucleophile-cleavable linker.
    Krueger, CA
    Chiu, BC
    Kelly, D
    Wolfe, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U143 - U143
  • [10] Solid-Phase Organic Synthesis of Difluoroalkyl Entities using a Novel Fluorinating Cleavage Strategy: Part 1. Linker Development: Scope and Limitations
    Wiehn, Matthias S.
    Lindell, Stephen D.
    Braese, Stefan
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (06): : 960 - 981
123