SYNTHESIS OF 6-EPI-N-ACETYL-D-NEURAMINIC AND 4,6-BISEPI-N-ACETYL-D-NEURAMINIC ACID BY ALDOL CONDENSATION

被引：12
|
作者：
MACK, H [1 ]
BROSSMER, R [1 ]
机构：
[1] UNIV HEIDELBERG,INST BIOCHEM 2,IM NEUENHEIMER FELD 328,W-6900 HEIDELBERG,GERMANY
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 14期
关键词：
NEURAMINIC ACID ANALOGS; ALDOL CONDENSATION; CHAIN ELONGATION; OXAZOLINE-FURANOSES;
D O I：
10.1016/S0040-4039(00)74163-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of allofurano-2,3-oxazoline 2 with potassium ditert.butyl oxaloacetate afforded the two diastereomeric compounds 3 and 3a which, after deblocking and alkaline treatment, are converted to the two epimeric sialic acids 5 and 5a.
引用
收藏
页码：1867 / 1870
页数：4
相关论文
共 50 条
  • [31] SIALIDOSIS - DIAGNOSIS WITH 4-METHYLUMBELLIFERYL-N-ACETYL-NEURAMINIC ACID
    WARNER, TG
    OBRIEN, JS
    CLINICAL RESEARCH, 1979, 27 (01): : A102 - A102
  • [32] Alkaline biocatalysis for the direct synthesis of N-acetyl-D-neuraminic acid (Neu5Ac) from N-acetyl-D-glucosamine (GlcNAc)
    Blayer, S
    Woodley, JM
    Dawson, MJ
    Lilly, MD
    BIOTECHNOLOGY AND BIOENGINEERING, 1999, 66 (02) : 131 - 136
  • [33] Biotechnological production and applications of N-acetyl-d-neuraminic acid: current state and perspectives
    Fei Tao
    Yinan Zhang
    Cuiqing Ma
    Ping Xu
    Applied Microbiology and Biotechnology, 2010, 87 : 1281 - 1289
  • [34] Biotechnological production and applications of N-acetyl-d-neuraminic acid: current state and perspectives
    Tao, Fei
    Zhang, Yinan
    Ma, Cuiqing
    Xu, Ping
    APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2010, 87 (04) : 1281 - 1289
  • [35] H-1-NMR INVESTIGATIONS ON THE MUTAROTATION OF N-ACETYL-D-NEURAMINIC ACID
    FRIEBOLIN, H
    SUPP, M
    BROSSMER, R
    KEILICH, G
    ZIEGLER, D
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1980, 19 (03) : 208 - 209
  • [36] C-13 STUDIES ON ANOMERIC KETOSIDES OF N-ACETYL-D-NEURAMINIC ACID
    ESCHENFELDER, V
    BROSSMER, R
    FRIEBOLIN, H
    TETRAHEDRON LETTERS, 1975, (35) : 3069 - 3072
  • [37] SYNTHESIS OF N-ACETYL-3-FLUORO-NEURAMINIC ACIDS
    NAKAJIMA, T
    HORI, H
    OHRUI, H
    MEGURO, H
    IDO, T
    AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1988, 52 (05): : 1209 - 1215
  • [38] PARTIAL ACETYLATION OF N-ACETYL AND N-GLYCOLYL NEURAMINIC ACID
    OGURA, H
    FURUHATA, K
    ANAZAWA, K
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1987, 76 (11) : S245 - S245
  • [39] Production of N-Acetyl-D-Neuraminic Acid by Use of an Efficient Spore Surface Display System
    Xu, Xiaoman
    Gao, Chao
    Zhang, Xifeng
    Che, Bin
    Ma, Cuiqing
    Qiu, Jianhua
    Tao, Fei
    Xu, Ping
    APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2011, 77 (10) : 3197 - 3201
  • [40] Development of an Escherichia coli-based biocatalytic system for the efficient synthesis of N-acetyl-D-neuraminic acid
    Chen, Xianzhong
    Zhou, Junbo
    Zhang, Lihua
    Pu, Zhongji
    Liu, Liming
    Shen, Wei
    Fan, You
    METABOLIC ENGINEERING, 2018, 47 : 374 - 382
12345