Synthesis of naphthoxylosides on solid support

被引：13
作者：
Jacobsson, M [1 ]
Ellervik, U [1 ]
机构：
[1] Lund Univ, Ctr Chem & Chem Engn, SE-22100 Lund, Sweden
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 37期
关键词：
xylosides; dihydroxynaphthalenes; antiproliferative; solid support;
D O I：
10.1016/S0040-4039(02)01467-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In order to investigate the selective antiproliferative effects shown by 2-(6-hydroxynaphthyl)-beta-D-xylopyranoside the 14 possible beta-D-xylopyranosidic compounds were synthesized on solid support. An aminomethylated polystyrene resin was converted into an acid chloride resin and then esterified using dihydroxynaphthalene. The free hydroxy group was then xylosylated Under BF3.OEt2 mediated conditions. The xyloside was deprotected and simultaneously cleaved off the resin Using NaOMe/MeOH. Final purification using reverse phase HPLC gave the pure xylosides in 6-42% yield with Virtually no formation of alpha-xylosides. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：6549 / 6552
页数：4
相关论文
共 11 条
  • [1] A versatile solid phase synthesis of lavendustin A and certain biologically active analogs
    Devraj, R
    Cushman, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9368 - 9373
  • [2] Erdmann H., 1888, LIEBIGS ANN CHEM, V247, P306, DOI [10.1002/jlac.18882470305, DOI 10.1002/JLAC.18882470305]
  • [3] FRITZ TA, 1994, J BIOL CHEM, V269, P300
  • [4] LEZNOFF CC, 1977, CAN J CHEM, V55, P3351
  • [5] Mani K, 1998, CANCER RES, V58, P1099
  • [6] OKAYAMA M, 1973, J BIOCHEM-TOKYO, V74, P1069
  • [7] EFFICIENT SYNTHESIS OF NON-K-REGION TRANS-DIHYDRO DIOLS OF POLYCYCLIC AROMATIC-HYDROCARBONS FROM ORTHO-QUINONES AND CATECHOLS
    PLATT, KL
    OESCH, F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (02) : 265 - 268
  • [8] The synthesis of 1,8-dihydroxynaphthalene-derived natural products:: palmarumycin CP1, palmarumycin CP2, palmarumycin C11, CJ-12,371, deoxypreussomerin A and novel analogues
    Ragot, JP
    Steeneck, C
    Alcaraz, ML
    Taylor, RJK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08): : 1073 - 1082
  • [9] XYLOSYLATION - THE FIRST STEP IN SYNTHESIS OF PROTEOGLYCAN
    SCHWARTZ, NB
    [J]. TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 1995, 7 (37) : 429 - 445
  • [10] BETA-D-XYLOSIDES AND THEIR ANALOGS AS ARTIFICIAL INITIATORS OF GLYCOSAMINOGLYCAN CHAIN SYNTHESIS - AGLYCONE-RELATED VARIATION IN THEIR EFFECTIVENESS INVITRO AND INOVO
    SOBUE, M
    HABUCHI, H
    ITO, K
    YONEKURA, H
    OGURI, K
    SAKURAI, K
    KAMOHARA, S
    UENO, Y
    NOYORI, R
    SUZUKI, S
    [J]. BIOCHEMICAL JOURNAL, 1987, 241 (02) : 591 - 601
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