(R)-2-[(2R,3S)-3-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranylmethyl]-4-benzyloxy-butyric acid methyl ester | 205865-97-0

• 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: (R)-2-[(2R,3S)-3-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranylmethyl]-4-benzyloxy-butyric acid methyl ester
• 英文别名: methyl (2R)-2-[[(2R,3S)-3-[(4R,5R)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]oxiran-2-yl]methyl]-4-phenylmethoxybutanoate
• CAS: 205865-97-0
• 化学式: C₂₁H₂₉N₃O₆
• 分子量: 419.478
• InChiKey: XBTWIBJFJZRNAZ-IEWDOMPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-[(2R,3S)-3-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranylmethyl]-4-benzyloxy-butyric acid methyl ester 在 palladium dihydroxide 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以13%的产率得到(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：

  (1S)-1-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 在 三(2-氯乙基)胺 、 丙酸 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 2.0h， 生成 (R)-2-[(2R,3S)-3-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranylmethyl]-4-benzyloxy-butyric 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

文献信息

• Synthesis and mannosidase inhibitory activity of 6- and 7-substituted analogs of swainsonine
  作者：William H Pearson、Erik J Hembre

  DOI：10.1016/s0040-4039(01)01778-6

  日期：2001.11

  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.