Acetic acid (2R,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester | 324740-33-2

• 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: Acetic acid (2R,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester
• 英文别名: [(2R,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-16-oxo-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxoheptyl] acetate
• CAS: 324740-33-2
• 化学式: C₄₅H₆₂O₅Si
• 分子量: 711.07
• InChiKey: QBOUHZIRZIWBEV-MEURGNNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  51
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester 在 sodium azide 、 potassium carbonate 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (3S,8S,9S,10R,13S,14S,17R)-17-[(2S,6R)-7-azido-6-methyl-3-oxoheptan-2-yl]-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one
  参考文献：
  名称：

  Total synthesis of solamargine

  摘要：

  Solamargine, (25R)-3 beta-{O-alpha-L-rhamnopyranosyl-(1 -> 2)-[O-alpha-L-rhamnopyranosyl-(1 -> 4)]-beta-D-glucopyranosyloxy}-22 alpha-N-spirosol-5-ene, has been synthesized in 13 steps in a 10.5% overall yield starting from the naturally abundant diosgenin. Condensation of a partially protected glucopyranosyl donor with an oxaza-spiro moiety, which was formed in one-pot azido reduction, significantly improved the synthesis of desired molecule. The target compound exhibited good cytotoxic activities against tumor cells HeLa, A549, MCF-7, K562, HCT116, U87, and HepG2 with IC(50) ranging from 2.1 to 8.0 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.064
• 作为产物：
  描述：

  (25R)-3β-tert-butyldiphenylsilyloxy-spirostan-5-ene 在 Oxone 、 碳酸氢钠 、 potassium iodide 、 锌 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 48.0h， 生成 Acetic acid (2R,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester
  参考文献：
  名称：

  Chemical Intertransformations of Diverse Bisdesmosidic Furostanol Saponins

  摘要：

  针对四种双糖基二萜皂苷，开发了一种有效的合成路线，并设计合成了36种衍生物，用于抗肿瘤研究。根据E环结构，讨论了这些呋喃固醇结构的化学互变过程。

  DOI：

  10.1246/cl.2007.214

文献信息

• The first synthetic route to furostan saponins
  作者：Biao Yu、Jianchun Liao、Jianbo Zhang、Yongzheng Hui

  DOI：10.1016/s0040-4039(00)01889-x

  日期：2001.1

  26-O-beta -D-Glucopyranosyl-22-methoxy-25(R)-furost-5-en-3 beta -ol 3-O-beta -D-glucopyranoside is synthesized from diosgenin in 11 steps and 26% overall yield. The present synthetic route represents the first one to furostan saponins. (C) 2000 Elsevier Science Ltd. All rights reserved.