Synthesis of 6-deoxy-homoDMDP and its C(5)-epimer:: absolute stereochemistry of natural products from Hyacinthus orientalis

被引：18
作者：
Behr, JB [1 ]
Guillerm, G [1 ]
机构：
[1] UFR Sci, Lab Chim Bioorgan, UMR 6519, F-51687 Reims 2, France
来源：
TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 02期
关键词：
D O I：
10.1016/S0957-4166(02)00081-2
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A concise enantioselective synthesis of 2,5-imino-2,5,6-trideoxy-D-manno-heptitol (6-deoxy-homoDMDP) and 2,5-imino-2,5,6-trideoxy-L-gulo-heptitol has been achieved. These compounds were used as stereochemical references to establish the absolute configuration of the corresponding naturally occurring stereoisomers, recently isolated from Hyacinthus orientalis. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：111 / 113
页数：3
相关论文
共 14 条
  • [1] Alkaloidal sugar mimetics: Biological activities and therapeutic applications
    Asano, N
    [J]. JOURNAL OF ENZYME INHIBITION, 2000, 15 (03): : 215 - 234
  • [2] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application
    Asano, N
    Nash, RJ
    Molyneux, RJ
    Fleet, GWJ
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (08) : 1645 - 1680
  • [3] Novel α-L-fucosidase inhibitors from the bark of Angylocalyx pynaertii (Leguminosae)
    Asano, N
    Yasuda, K
    Kizu, H
    Kato, A
    Fan, JQ
    Nash, RJ
    Fleet, GWJ
    Molyneux, RJ
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 2001, 268 (01): : 35 - 41
  • [4] Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis
    Asano, N
    Kato, A
    Miyauchi, M
    Kizu, H
    Kameda, Y
    Watson, AA
    Nash, RJ
    Fleet, GWJ
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05): : 625 - 628
  • [5] Inhibition of chitin synthetase from Saccharomyces cerevisiae by a new UDP-GlcNAc analogue
    Behr, JB
    Gautier-Lefebvre, I
    Mvondo-Evina, C
    Guillerm, G
    Ryder, NS
    [J]. JOURNAL OF ENZYME INHIBITION, 2001, 16 (02): : 107 - 112
  • [6] GLYCOSIDASE INHIBITION BY PLANT ALKALOIDS WHICH ARE STRUCTURAL ANALOGS OF MONOSACCHARIDES
    EVANS, SV
    FELLOWS, LE
    SHING, TKM
    FLEET, GWJ
    [J]. PHYTOCHEMISTRY, 1985, 24 (09) : 1953 - 1955
  • [7] ENANTIOSPECIFIC SYNTHESES OF DEOXYMANNOJIRIMYCIN, FAGOMINE AND 2R,5R-DIHYDROXYMETHYL-3R,4R-DIHYDROXYPYRROLIDINE FROM D-GLUCOSE
    FLEET, GWJ
    SMITH, PW
    [J]. TETRAHEDRON LETTERS, 1985, 26 (11) : 1469 - 1472
  • [8] INHIBITION OF HIV REPLICATION BY AMINO-SUGAR DERIVATIVES
    FLEET, GWJ
    KARPAS, A
    DWEK, RA
    FELLOWS, LE
    TYMS, AS
    PETURSSON, S
    NAMGOONG, SK
    RAMSDEN, NG
    SMITH, PW
    SON, JC
    WILSON, F
    WITTY, DR
    JACOB, GS
    RADEMACHER, TW
    [J]. FEBS LETTERS, 1988, 237 (1-2) : 128 - 132
  • [9] THE USE OF GRIGNARD-REAGENTS IN THE SYNTHESIS OF CARBOHYDRATES .3. THE ONE-WAY ANOMERIZATION OF METHYL GLYCOFURANOSIDES AND THE OPENING OF THEIR FURANOSE RINGS
    KAWANA, M
    KUZUHARA, H
    EMOTO, S
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (05) : 1492 - 1504
  • [10] LAFERLA B, 2000, IMINOSUGARS GLYCOSID, P68
12