(1S,2S,4R,5S)-4-[(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxycarbonyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester | 221344-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4R,5S)-4-[(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxycarbonyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
• CAS: 221344-11-2
• 化学式: C₃₆H₅₅NO₁₈
• 分子量: 789.829
• InChiKey: OUKWBJKIGMGRPW-HDBNGZKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  55.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  251.89
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5S)-4-[(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxycarbonyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 、 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-acetylamino-2-(2,2-dimethyl-propionyloxymethyl)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以30%的产率得到ditert-butyl (1S,2S,4R,5S)-4-[(2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-2-yl]oxy-5-[(2R,3R,4R,5R,6R)-3-acetamido-5-(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxycyclohexane-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of a Pseudo Tetrasaccharide Mimic of Ganglioside GM1

  摘要：

  The pseudo tetrasaccharide 2 was designed to mimic ganglioside GM1, the membrane receptor of both the cholera toxin and of the heat-labile toxin of E. coli. Compound 2 retains the Gal and Neu5Ac recognition determinant of GM1 and uses as the scaffold element a new, conformationally restricted cyclohexanediol (DCCHD 3), with the same relative and absolute configuration of natural galactose; The diol 3 was enantioselectively synthesized by an asymmetric Diels-Alder reaction, followed by dihydroxylation of the resulting cyclohexene. Glycosylation of 3 with the sialyl donor 17 and the Gal beta(l-3)GalNAc donor 15, followed by removal of the protecting groups, completed the synthesis of 2.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1311::aid-ejoc1311>3.0.co;2-w
• 作为产物：
  描述：

  (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid di-tert-butyl ester 在 osmium (III) chloride 、 十二/十四烷基二甲基氧化胺 、 三氟甲磺酸三甲基硅酯 作用下， 生成 (1S,2S,4R,5S)-4-[(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxycarbonyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  糖模拟物：霍乱毒素的人工受体

  摘要：

  该论文描述了伪糖 2 [Galβ1−3GalNAcβ1−4(NeuAcα2−3)DCCHD]，一种霍乱毒素 (CT) 的高亲和力结合剂。该分子是使用分子建模技术设计的，以模拟天然 CT 膜受体神经节苷脂 GM1。GM1 的中心残基是一个 3,4-二取代的半乳糖单元，被认为是神经节苷脂支架元件，并被构象锁定的环己二醇 (DCCHD) 取代。DCCHD 使用对映选择性 Diels Alder 方法和在赤道位置的区域选择性 α-唾液酸化以对映纯形式合成。用Galβ(1-3)GalNAc供体进行糖基化完成了2的合成。发现2的溶液结构及其与CT的结合能力类似于GM1寡糖的那些。

  DOI：

  10.1021/ja983567c

文献信息

• Mimics of ganglioside GM1 as cholera toxin ligands: replacement of the GalNAc residueElectronic supplementary information (ESI) available: synthetic details, product characterisations and full NOE contact list. See http://www.rsc.org/suppdata/ob/b2/b210503a/
  作者：Anna Bernardi、Daniela Arosio、Leonardo Manzoni、Diego Monti、Helena Posteri、Donatella Potenza、Silvia Mari、Jesús Jiménez-Barbero

  DOI：10.1039/b210503a

  日期：2003.2.27

  Two new cholera toxin (CT) ligands (4 and 5) are described. The new ligands were designed starting from the known GM1 mimics 2 and 3 by replacement of their GalNAc residue with the C4 isomer GlcNAc. As predicted by molecular modelling, the conformational properties of the equivalent pairs 2–4 and 3–5 are very similar and their affinity for CT is of the same order of magnitude. NMR experiments have also proved that 5 occupies the GM1-binding site of the toxin and have revealed its bound conformation.

  描述了两种新的霍乱毒素（CT）配体（4和5）。这两种新配体是从已知的GM1类似物2和3开始设计的，通过将它们的GalNAc残基替换为C4异构体GlcNAc。根据分子建模预测，等价对2-4和3-5的构象特性非常相似，它们对CT的亲和力也在同一数量级。NMR实验也证实了5占据毒素的GM1结合位点，并揭示了其结合构象。