(E)-2-(2-Benzyloxy-ethyl)-5-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-enoic acid methyl ester | 205865-94-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-(2-Benzyloxy-ethyl)-5-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-enoic acid methyl ester
• 英文别名: methyl (E)-5-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(2-phenylmethoxyethyl)pent-4-enoate
• CAS: 205865-94-7
• 化学式: C₂₁H₃₀O₆
• 分子量: 378.466
• InChiKey: VPUFDADBJZQTJZ-POXITBOHSA-N

物化性质

• 沸点：
  499.9±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-Benzyloxy-ethyl)-5-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-enoic acid methyl ester 在 palladium dihydroxide 三(2-氯乙基)胺 、 氢气 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 生成 (3aR,7R,9R,9aR,9bS)-7-(2-Benzyloxy-ethyl)-9-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]indolizin-6-one
  参考文献：
  名称：

  Synthesis and mannosidase inhibitory activity of 6- and 7-substituted analogs of swainsonine

  摘要：

  Swainsonine (1), an inhibitor of the important glycoprotein-processing enzyme Golgi alpha -mannosidase II, is a clinical candidate for cancer treatment. Analogs bearing substituents at C-6 and C-7 have been prepared and evaluated as inhibitors of alpha -mannosidase (jack bean), a closely related enzyme. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01778-6
• 作为产物：
  描述：

  (E)-2-(2-Benzyloxy-ethyl)-5-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pent-4-enoic acid methyl ester 在 n-Bu₄F 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-2-(2-Benzyloxy-ethyl)-5-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis and mannosidase inhibitory activity of 6- and 7-substituted analogs of swainsonine

  摘要：

  Swainsonine (1), an inhibitor of the important glycoprotein-processing enzyme Golgi alpha -mannosidase II, is a clinical candidate for cancer treatment. Analogs bearing substituents at C-6 and C-7 have been prepared and evaluated as inhibitors of alpha -mannosidase (jack bean), a closely related enzyme. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01778-6