Synthesis of the sialic acid (-)-KDN and certain epimers from (-)-3-dehydroshikimic acid or (-)-quinic acid

被引:15
|
作者
Banwell, MG [1 ]
Hungerford, NL [1 ]
Jolliffe, KA [1 ]
机构
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
关键词
D O I
10.1021/ol049048y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(-)-3-Dehydroshikimic acid (3-DHS, 4), a C-7-building block now available in large quantity from corn syrup, has been converted into the sialic acid (-)-KDN (3) as well as its C-7- and C-8-epimers. (-)-Quinic acid can be used for the same purpose.
引用
收藏
页码:2737 / 2740
页数:4
相关论文
共 50 条
  • [41] Synthesis of Phosphonic Acid Analogues of Sialic Acids (Neu5Ac and KDN) as Potential Sialidase Inhibitors
    Chan, T.-H.
    Xin, Y.-C.
    Journal of Organic Chemistry, 62 (11):
  • [42] Synthesis of phosphonic acid analogues of sialic acids (Neu5Ac and KDN) as potential sialidase inhibitors
    Chan, TH
    Xin, YC
    vonItzstein, M
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11): : 3500 - 3504
  • [43] BIOLOGICAL SYNTHESIS OF 5-DEHYDROSHIKIMIC ACID BY A PLANT EXTRACT
    NANDY, M
    GANGULI, NC
    BIOCHIMICA ET BIOPHYSICA ACTA, 1961, 48 (03) : 608 - &
  • [44] SYNTHESIS OF 3-0-O.COUMARYL-D-(-)-QUINIC, 4-O-O.COUMARYL-D-(-)-QUINIC AND 3-O-FERULYL-D-(-)-QUINIC ACID - IMPROVED SYNTHESIS OF 3-O-SINAPYL-D-(-)-QUINIC ACID
    DEPOOTER, H
    DEBRUCKER, J
    VANSUMERE, CF
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1976, 85 (09): : 663 - 671
  • [45] ENANTIOSPECIFIC SYNTHESIS OF INOSITOL POLYPHOSPHATES, PHOSPHATIDYLINOSITIDES, AND ANALOGS FROM (-)-QUINIC ACID
    FALCK, JR
    ABDALI, A
    ACS SYMPOSIUM SERIES, 1991, 463 : 145 - 154
  • [46] Synthesis of a New Family of Aminocyclitols from D-(-)-Quinic Acid
    Shih, Tzenge-Lien
    Li, Heng-Yi
    Ke, Ming-Shin
    Kuo, Wei-Shen
    SYNTHETIC COMMUNICATIONS, 2008, 38 (23) : 4139 - 4149
  • [47] cis-decalins from quinic acid:: Toward a synthesis of branimycin
    Marchart, Stefan
    Mulzer, Johann
    Enev, Valentin S.
    ORGANIC LETTERS, 2007, 9 (05) : 813 - 816
  • [48] Progress in the Synthesis of Sialic Acid Derivatives
    Wang, Ruyi
    Zhang, Shu
    Tan, Yanhong
    Hong, Weiyao
    Cheng, Bo
    Chen, Qingxin
    Zhu, Yuntao
    Feng, Lianshun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (03) : 461 - 474
  • [49] Synthesis and study of sialic acid analogs
    Ward, George
    France, Stefan
    Liotta, Charles
    Krishnamurthy, Ramanarayanan
    Hud, Nicholas
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [50] SYNTHESIS OF N-ACETYLNEURAMINIC ACID (LACTAMINIC ACID, O-SIALIC ACID)
    CORNFORTH, JW
    DAINES, ME
    GOTTSCHALK, A
    PROCEEDINGS OF THE CHEMICAL SOCIETY OF LONDON, 1957, (01): : 25 - 26