(Z)-(S)-5-Benzyloxy-1-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pent-2-en-1-ol | 205866-40-6

• 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: (Z)-(S)-5-Benzyloxy-1-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pent-2-en-1-ol
• 英文别名: (Z,1S)-1-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-5-phenylmethoxypent-2-en-1-ol
• CAS: 205866-40-6
• 化学式: C₂₄H₄₀O₅Si
• 分子量: 436.664
• InChiKey: TVZILOUEEADENC-ZEQOJMHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-(S)-5-Benzyloxy-1-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pent-2-en-1-ol 在 三(2-氯乙基)胺 、 四丁基氟化铵 、 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 (S)-3-[3-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-5-benzyloxy-pentanoic 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
• 作为产物：
  描述：

  2,3-O-isopropylidene-D-erythrose 在 Pd-BaSO₄ 咪唑 、 氢气 作用下， 生成 (Z)-(S)-5-Benzyloxy-1-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pent-2-en-1-ol
  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.