(1S,2S,4R,5S)-4-Benzyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester | 231278-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,4R,5S)-4-Benzyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (1S,2S,4S,5R)-4-hydroxy-5-phenylmethoxycyclohexane-1,2-dicarboxylate
• CAS: 231278-93-6
• 化学式: C₂₃H₃₄O₆
• 分子量: 406.519
• InChiKey: PKEPGAHXYMWRHD-CADBVGFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5S)-4-Benzyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 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：

  (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 、 四丁基碘化铵 、 二正丁基氧化锡 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 9.0h， 生成 (1S,2S,4R,5S)-4-Benzyloxy-5-hydroxy-cyclohexane-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

• 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.