(25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxycholest-5-ene-16,22-dione | 886976-10-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxycholest-5-ene-16,22-dione
• CAS: 886976-10-9
• 化学式: C₃₅H₅₈O₅Si
• 分子量: 586.928
• InChiKey: BEXKZISSWYTLIJ-ACKDUNQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxycholest-5-ene-16,22-dione 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  胆甾烷和呋甾皂苷类似物的合成及皂苷元C-22绝对构型的测定

  摘要：

  首次建立并采用了一种简便有效的合成胆甾烷和呋甾皂苷类似物的方法。遵循这一策略，从薯蓣皂苷元开始，三种新型胆甾烷皂苷类似物：(22S,25R)-3β,22,26-trihydroxy-cholest-5-ene-16-one 22-O-[O-α-L-rhamnopyranosyl- (1→2)-β-D-吡喃葡萄糖苷] 11, (25R)-3β,16β,26-trihydroxy-cholest-5-ene-22-one 16-O-[O-α-L-rhamnopyranosyl-(1 →2)-α-D-吡喃葡萄糖苷] 14 和 (25R)-3β,16β,26-trihydroxy-cholest-5-ene-22-one 16-O-[O-α-L-rhamnopyranosyl-(1→2 )-β-D-吡喃葡萄糖苷] 17、三种新型呋喃坦皂苷类似物：(22S,25R)-furost-5-ene-3β,22

  DOI：

  10.1016/j.steroids.2010.07.011
• 作为产物：
  描述：

  diosgenyl 3-O-tert-butyldimethylsilyl ether 在 碳酸氢钠 、 溶剂黄146 、 potassium iodide 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 以17.3 g的产率得到(25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxycholest-5-ene-16,22-dione
  参考文献：
  名称：

  Synthesis and cytotoxicities of icogenin analogues with disaccharide residues

  摘要：

  For further structure-activity relationships (SAR) research of furostan saponin, two icogenin analogues: (25R)-22-O-methyl-furost-5-en-3 beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranoside 1 and (25R)-22-O-methyl-furost-5-en-3 beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-glucopyranoside 2, with valuable disaccharide moieties, were synthesized from diosgenin through eight steps. Both of the analogues behaved the similar cytotoxic activities with icogenin, towards nine types of human tumor cells herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.092

文献信息

• Synthesis of cholestane glycosides bearing OSW-1 disaccharide or its 1→4-linked analogue and their antitumor activities
  作者：Dan Zheng、Liang Zhou、Yuyao Guan、Xiaozhuo Chen、Wanqi Zhou、Xiaoguang Chen、Pingsheng Lei

  DOI：10.1016/j.bmcl.2010.07.085

  日期：2010.9

  For further structure-activity relationship (SAR) research of OSW saponins, a cholestane glycoside, namely 3 beta, 16 beta, 26-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-xylopyranosyl)-(1 -> 3)-2-O- acetyl-alpha-L-arabinopyranoside (1) together with two 1 -> 4-linked disaccharide analogues (2 and 3) were synthesized. Their cytotoxic activities were evaluated by the standard MTT assay. Compound 1 showed potent cytotoxicity against five types of human tumor cells, with IC50 ranging between 1.3 and 73 nM. (c) 2010 Elsevier Ltd. All rights reserved.