ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-β-D-galactopyranoside | 139209-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-β-D-galactopyranoside
• 英文别名: [(2S,4aR,6S,7R,8S,8aS)-8-(2-chloroacetyl)oxy-6-ethylsulfanyl-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 139209-48-6
• 化学式: C₂₄H₂₅ClO₇S
• 分子量: 492.977
• InChiKey: WKEIPTZVRMKNNK-BEVQEULBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-β-D-galactopyranoside 在 2,6-二甲基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 硫脲 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 tetradecyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  立体选择性合成的低聚α-（2,8）-3-脱氧-D-甘露聚糖-2-辛磺酸衍生物。

  摘要：

  DOI：

  10.1002/anie.200503299
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Higson, Adrian P.; Tsvetkov, Yury E.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1998, # 16, p. 2587 - 2595

  摘要：

  DOI：

文献信息

• Synthesis and Molecular Recognition Studies of the HNK-1 Trisaccharide and Related Oligosaccharides. The Specificity of Monoclonal Anti-HNK-1 Antibodies as Assessed by Surface Plasmon Resonance and STD NMR
  作者：Yury E. Tsvetkov、Monika Burg-Roderfeld、Gabriele Loers、Ana Ardá、Elena V. Sukhova、Elena A. Khatuntseva、Alexey A. Grachev、Alexander O. Chizhov、Hans-Christian Siebert、Melitta Schachner、Jesús Jiménez-Barbero、Nikolay E. Nifantiev

  DOI：10.1021/ja2083015

  日期：2012.1.11

  The human natural killer cell carbohydrate, HNK-1, plays function-conducive roles in peripheral nerve regeneration and synaptic plasticity. It is also the target of autoantibodies in polyneuropathies. It is thus important to synthesize structurally related HNK-1 carbohydrates for optimizing its function-conducive roles, and for diagnosis and neutralization of autoantibodies in the fatal Guillain-Barre syndrome. As a first step toward these goals, we have synthesized several HNK-1 carbohydrate derivatives to assess the specificity of monoclonal HNK-1 antibodies from rodents: 2-aminoethyl glycosides of selectively O-sulfated trisaccharide corresponding to the HNK-1 antigen, its nonsulfated analogue, and modified structures containing 3-O-fucosyl or 6-O-sulfo substituents in the N-acetylglucosamine residues. These were converted, together with several related oligosaccharides, into biotin-tagged probes to analyze the precise carbohydrate specificity of two anti-HNK-1 antibodies by surface plasmon resonance that revealed a crucial role of the glucuronic acid in antibody binding. The contribution of the different oligosaccharide moieties in the interaction was shown by saturation transfer difference (STD) NMR of the complex consisting of the HNK-1 pentasaccharide and the HNK-1 412 antibody.
• Stereoselective Synthesis of Oligo-α(2,8)-3-deoxy-D-manno-2-octulosonic Acid Derivatives
  作者：Hiroshi Tanaka、Daisuke Takahashi、Takashi Takahashi

  DOI：10.1002/anie.200503299

  日期：2006.1.23
• Higson, Adrian P.; Tsvetkov, Yury E.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1998, # 16, p. 2587 - 2595
  作者：Higson, Adrian P.、Tsvetkov, Yury E.、Ferguson, Michael A. J.、Nikolaev, Andrei V.

  DOI：——

  日期：——