Solid-phase intermolecular radical reactions 2:: Synthesis of C-glycopeptide mimetics via a novel acrylate acceptor

被引：30

作者：

Caddick, S ^{[1
]}

Hamza, D ^{[1
]}

Wadman, SN ^{[1
]}

Wilden, JD ^{[1
]}

机构：

[1] Univ Sussex, Chem Lab, Ctr Biomol Design & Drug Dev, Brighton BN1 9QJ, E Sussex, England

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 10期

关键词：

D O I：

10.1021/ol025846h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel tetrafluorophenol-linked acrylate is reported as an activated acceptor for intermolecular radical reactions. Addition of alkyl radicals led to pure products in good yields. We include here the first syntheses of C1- and C6-linked glycosides using a solid-phase radical methodology.

引用

页码：1775 / 1777

页数：3

共 50 条

[41] Solid-phase synthesis of isoindolines via a rhodium-catalyzed [2+2+2] cycloaddition
Sun, Q
Zhou, XM
Islam, K
Kyle, DJ
TETRAHEDRON LETTERS, 2001, 42 (37) : 6495 - 6497
[42] BUILDING-BLOCKS FOR SOLID-PHASE GLYCOPEPTIDE SYNTHESIS - 2-ACETAMIDO-2-DEOXY-BETA-D-GLYCOSIDES OF FMOCSEROH AND FMOCTHROH
ARSEQUELL, G
KRIPPNER, L
DWEK, RA
WONG, SYC
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) : 2383 - 2384
[43] Synthesis of C-linked antifreeze glycoprotein mimics via a convergent solid-phase approach.
Ben, RN
Eniade, A
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U172 - U172
[44] Solid-phase synthesis of 2-phenyl-4-quinolinone library via flavylium salt
Sato, S
Kubota, Y
Kumagai, H
Kumazawa, T
Matsuba, S
Onodera, J
Suzuki, M
HETEROCYCLES, 2000, 53 (07) : 1523 - 1532
[45] Solid-phase synthesis via N-terminal attachment to the 2-chlorotrityl resin
Hoekstra, WJ
Greco, MN
Yabut, SC
Hulshizer, BL
Maryanoff, BE
TETRAHEDRON LETTERS, 1997, 38 (15) : 2629 - 2632
[46] Convenient synthesis of Thr and Ser carrying the tumor associated sialyl-(2→3)-T antigen as building blocks for solid-phase glycopeptide synthesis
Komba, S
Meldal, M
Werdelin, O
Jensen, T
Bock, K
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04): : 415 - 419
[47] Depsipeptide methodology for solid-phase peptide synthesis:: Circumventing side reactions and development of an automated technique via depsidipeptide units
Coin, Irene
Doelling, Rudolf
Krause, Eberhard
Bienert, Michael
Beyermann, Michael
Sferdean, Calin Dan
Carpino, Louis A.
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16): : 6171 - 6177
[48] Novel pH indicator dyes for array preparation via NHS ester activation or solid-phase organic synthesis
Trupp, Sabine
Hoffmann, Patrick
Henkel, Thomas
Mohr, Gerhard J.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (23) : 4319 - 4322
[49] Novel, selective indole-based ECE inhibitors:: Lead optimization via solid-phase and classical synthesis
Brands, M
Ergüden, JK
Hashimoto, K
Heimbach, D
Schröder, C
Siegel, S
Stasch, JP
Weigand, S
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (19) : 4201 - 4205
[50] A novel resin linker for solid-phase peptide synthesis which call be cleaved using two sequential mild reactions
Zheng, AL
Shan, DX
Shi, XL
Wang, BH
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20): : 7459 - 7466

← 1 2 3 4 5 →