CONVENIENT SYNTHESES OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) AND 3-DEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID (KDN) DERIVATIVES FROM D-MANNOSE

被引:17
|
作者
SATO, K
MIYATA, T
TANAI, I
YONEZAWA, Y
机构
关键词
D O I
10.1246/cl.1994.129
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Homer-Wittig reactions of 4-O-benzyl-2,3:5,6-di-O-isopropylidene-D-mannose and 2,3,4,5,6,7-hexa-O-benzyl-6-D-glycero-2,3,4,5-D-galacto-heptose with methyl 2-benzyloxycarbonylamino-2-(diethoxyphosphoryl)acetate gave the corresponding alpha-dehydroamino acid derivatives in good yields, respectively. They were converted to methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-alpha-D-manno-2-octulopyranosonate and methyl (methyl 3-deoxy-D-glycero-beta-D-galacto-2-nonulopyranosid)onate via methyl alpha-oxoalkanoate derivatives
引用
收藏
页码:129 / 132
页数:4
相关论文
共 50 条
  • [31] NOVEL DISACCHARIDES CONTAINING 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) AND LIPID A SUBUNIT ANALOGS
    KISO, M
    FUJITA, M
    HAYASHI, E
    HASEGAWA, A
    UNGER, FM
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1987, 6 (04) : 691 - 696
  • [32] Characterization of a putative 3-deoxy-d-manno-2-octulosonic acid (Kdo) transferase gene from Arabidopsis thaliana
    Seveno, Martial
    Seveno-Carpentier, Emilie
    Voxeur, Aline
    Menu-Bouaouiche, Laurence
    Rihouey, Christophe
    Delmas, Frederic
    Chevalier, Christian
    Driouich, Azeddine
    Lerouge, Patrice
    GLYCOBIOLOGY, 2010, 20 (05) : 617 - 628
  • [33] The Aspergillus fumigatus Sialidase Is a 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid Hydrolase (KDNase) STRUCTURAL AND MECHANISTIC INSIGHTS
    Telford, Judith C.
    Yeung, Juliana H. F.
    Xu, Guogang
    Kiefel, Milton J.
    Watts, Andrew G.
    Hader, Stefan
    Chan, Jefferson
    Bennet, Andrew J.
    Moore, Margo M.
    Taylor, Garry L.
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2011, 286 (12) : 10783 - 10792
  • [34] DO ENDOTOXINS DEVOID OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID EXIST
    CAROFF, M
    LEBBAR, S
    SZABO, L
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 143 (03) : 845 - 847
  • [35] A STEREOCONTROLLED APPROACH TO 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONTAINING DISACCHARIDES
    HAUDRECHY, A
    SINAY, P
    TETRAHEDRON LETTERS, 1990, 31 (40) : 5765 - 5768
  • [36] Formal Synthesis of 3-Deoxy-D-manno-Octulosonic Acid (KDO) and 3-Deoxy-D-arabino-2-heptulosonic Acid (DAH)
    Pradhan, Tapan Kumar
    Lin, Chun Cheng
    Mong, Kwok Kong Tony
    SYNLETT, 2013, 24 (02) : 219 - 222
  • [37] SYNTHESES OF REPEATING UNITS OF ESCHERICHIA-COLI CAPSULAR POLYSACCHARIDES CONTAINING D-RIBOSE AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
    KOSMA, P
    SCHULZ, G
    UNGER, FM
    CARBOHYDRATE RESEARCH, 1984, 132 (02) : 261 - 274
  • [38] DIOXALANONES AS SYNTHETIC INTERMEDIATES .6. SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO), 3-DEOXY-D-ARABINO-2-HEPTULOSONIC ACID (DAH) AND 2-KETO-3-DEOXY-D-GLUCONIC ACID (KDG)
    RAMAGE, R
    MACLEOD, AM
    ROSE, GW
    TETRAHEDRON, 1991, 47 (29) : 5625 - 5636
  • [39] Benzyl Benzoate Glycoside and 3-Deoxy-D-manno-2-octulosonic Acid Derivatives from Solidago decurrens
    Shiraiwa, Ken
    Yuan, Shen
    Fujiyama, Ayako
    Matsuo, Yosuke
    Tanaka, Takashi
    Jiang, Zhi-Hong
    Kouno, Isao
    JOURNAL OF NATURAL PRODUCTS, 2012, 75 (01): : 88 - 92
  • [40] STEREOSELECTIVE TOTAL SYNTHESES OF THE NATURALLY-OCCURRING ENANTIOMERS OF N-ACETYLNEURAMINIC ACID AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID - A NEW AND STEREOSPECIFIC APPROACH TO SIALO AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONJUGATES
    DANISHEFSKY, SJ
    DENINNO, MP
    CHEN, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) : 3929 - 3940