(25R)-3β-tert-butyldiphenylsilyloxy-26-hydroxy-cholest-5-ene-16,22-dione

• 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)-3β-tert-butyldiphenylsilyloxy-26-hydroxy-cholest-5-ene-16,22-dione
• 英文别名: (3S,8S,9S,10R,13S,14S,17R)-3-[tert-butyl(diphenyl)silyl]oxy-17-[(2S,6R)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one
• 化学式: C₄₃H₆₀O₄Si
• 分子量: 669.033
• InChiKey: FQTHBFHTPPHGMD-NQWJMKFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  薯蓣皂素 在 咪唑 、 Oxone 、 碳酸氢钠 、 potassium carbonate 、 potassium iodide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 64.0h， 生成 (25R)-3β-tert-butyldiphenylsilyloxy-26-hydroxy-cholest-5-ene-16,22-dione
  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

• An Improved Synthesis of Methyl Protodioscin: Tautomerization and Direct Access to the 3-O-Substituted Kryptogenin
  作者：Qing-Chun Xu、Yang Liu、Jiao Liu、Chun-Xian He、Mao-Cai Yan、Mao-Sheng Cheng

  DOI：10.1246/cl.2008.780

  日期：2008.7.5

  The acid-catalyzed tautomerization of 3-O-substituted kryptogenin 2 was studied, and the effects of acids such as silica gel, TMSOTf, acetic acid, and CDCl3, are discussed. Additionally, a Zn/KI/HOAc reduction based on this tautomerization was adopted, which afforded 2 directly, and provided a facile procedure for the synthesis of methyl protodioscin and other furostanol saponins in a mild way.

  研究了酸催化的3-O取代的克里托吉宁（kryptogenin）2的互变异构化，并讨论了硅胶、三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）、乙酸和氘氯仿等酸的影响。此外，基于这种互变异构化，采用了Zn/KI/HOAc还原法，直接得到2，并提供了一种温和的方法来合成甲基原薯蓣皂苷和其他呋甾皂苷。
• 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.
• Total synthesis of solamargine
  作者：Guohua Wei、Jing Wang、Yuguo Du

  DOI：10.1016/j.bmcl.2011.03.064

  日期：2011.5

  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.
• Chemical Intertransformations of Diverse Bisdesmosidic Furostanol Saponins
  作者：Dong-Mei Zhao、Yang Liu、Yong-Xiang Liu、Li-Gang Zheng、Mao-Cai Yan、Mao-Sheng Cheng

  DOI：10.1246/cl.2007.214

  日期：2007.2

  An effective synthetic route towards four types of bisdesmosidic furostanol saponin was developed and 36 derivatives were designed and synthesized for antitumor investigation. The chemical intertransformations of these furostanol structures were discussed with respect to the E ring.

  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。