(1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid di-tert-butyl ester | 231278-92-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid di-tert-butyl ester
• CAS: 231278-92-5
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: OQJZJLAPLYRJDY-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid di-tert-butyl ester 在 palladium on activated charcoal 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 、 氢气 、 四丁基碘化铵 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 11.0h， 生成 ditert-butyl (1S,2S,4S,5R)-4-[(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]oxy-5-hydroxycyclohexane-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：

  Cyclohex-4-ene-1,2-dicarboxylic acid bis-((S)-1-ethoxycarbonyl-ethyl) ester 在 lithium hydroxide 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 24.0h， 生成 (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid di-tert-butyl ester
  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

文献信息

• Sugar Mimics:  An Artificial Receptor for Cholera Toxin
  作者：Anna Bernardi、Anna Checchia、Paola Brocca、Sandro Sonnino、Fabio Zuccotto

  DOI：10.1021/ja983567c

  日期：1999.3.1

  paper describes the pseudosugar 2 [Galβ1−3GalNAcβ1−4(NeuAcα2−3)DCCHD], a high affinity binder of cholera toxin (CT). The molecule was designed using molecular modeling techniques to mimic the natural CT membrane receptor, ganglioside GM1. The central residue of GM1, a 3,4-disubstituted galactose unit, was recognized as the ganglioside scaffold element and substituted with a conformationally locked cyclohexanediol

  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。
• Stereoselective Synthesis of Conformationally Constrained Cyclohexanediols:  A Set of Molecular Scaffolds for the Synthesis of Glycomimetics
  作者：Anna Bernardi、Daniela Arosio、Leonardo Manzoni、Fabrizio Micheli、Alessandra Pasquarello、Pierfausto Seneci

  DOI：10.1021/jo015570b

  日期：2001.9.1

  The practical, stereoselective synthesis of the three diastereoisomeric 1,2-trans-dicarboxy-4,5-cyclohexanediols. 1-3 (DCCHDs) is described, starting from a common precursor, easily available in both enantiomeric forms. The regioselective derivatization of all functional groups of I is also reported. The three DCCHDs are locked in a single chair conformation and thus can be used to mimic vicinally disubstituted monosaccharides of any relative configuration.