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
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
收藏
页码:1775 / 1777
页数:3
相关论文
共 18 条
  • [1] Glycomimetics: A programmed approach toward neoglycopeptide libraries
    Arya, P
    Kutterer, KMK
    Barkley, A
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (02): : 120 - 126
  • [2] Solid-phase intermolecular radical reactions 1. Sulfonyl radical addition to isolated alkenes and alkynes
    Caddick, S
    Hamza, D
    Wadman, SN
    [J]. TETRAHEDRON LETTERS, 1999, 40 (40) : 7285 - 7288
  • [3] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2.
    CURRAN, DP
    [J]. SYNTHESIS-STUTTGART, 1988, (07): : 489 - 513
  • [4] CURRAN DP, 1988, SYNTHESIS-STUTTGART, P419
  • [5] Synthesis of benzofuran derivatives on solid support via SmI2-mediated radical cyclization
    Du, XH
    Armstrong, RW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) : 5678 - 5679
  • [6] Free radical allyl transfers utilizing soluble non-cross-linked polystyrene and carbohydrate scaffold supports
    Enholm, EJ
    Gallagher, ME
    Jiang, SJ
    Batson, WA
    [J]. ORGANIC LETTERS, 2000, 2 (21) : 3355 - 3357
  • [7] A general synthesis of structurally diverse building blocks for preparing analogues of C-linked antifreeze glycoproteins
    Eniade, A
    Murphy, AV
    Landreau, G
    Ben, RN
    [J]. BIOCONJUGATE CHEMISTRY, 2001, 12 (05) : 817 - 823
  • [8] FORMATION OF CC BONDS BY ADDITION OF FREE-RADICALS TO ALKENES
    GIESE, B
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (10): : 753 - 764
  • [9] SYNTHESES WITH RADICALS-C-C BOND FORMATION VIA ORGANOTIN AND ORGANOMERCURY COMPOUNDS
    GIESE, B
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (07): : 553 - 565
  • [10] Giese B., 1986, RADICALS ORGANIC SYN