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-phenylmethoxycyclohexane-1,2-dicarboxylate | 231278-96-9

• 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: 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-phenylmethoxycyclohexane-1,2-dicarboxylate
• CAS: 231278-96-9
• 化学式: C₅₅H₈₁NO₂₂
• 分子量: 1108.24
• InChiKey: VOCRBKDHGMFGQL-MZANMHCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  78
• 可旋转键数：
  30
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  286
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  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-phenylmethoxycyclohexane-1,2-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以73%的产率得到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：

  ditert-butyl (1S,2S,4S,5R)-4,5-dihydroxycyclohexane-1,2-dicarboxylate 在 三氟甲磺酸三甲基硅酯 、 四丁基碘化铵 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 10.0h， 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-phenylmethoxycyclohexane-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