(25R)-2α-hydroxy-5α-spirostan-3-one | 848854-25-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25R)-2α-hydroxy-5α-spirostan-3-one
• CAS: 848854-25-1
• 化学式: C₂₇H₄₂O₄
• 分子量: 430.628
• InChiKey: XTRIWNXILWIYSZ-QUHQOQEASA-N

物化性质

• 沸点：
  548.9±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  31.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (25R)-2α-hydroxy-5α-spirostan-3-one 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,2-双(二苯基膦)乙烷 吡啶 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 33.08h， 生成 (25R)-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan-2-one
  参考文献：
  名称：

  Preparation of an analogue of orbicuside A, an unusual cardiac glycoside

  摘要：

  A steroid containing a multi-linked glycoside, analogous to the bufadienolide orbicuside A, has been prepared. The key steps were (i) the preparation of a 2alpha-allyloxycarbonyloxy-3beta-hydroxy steroid, (ii) a Ferrier reaction between the steroid and a rhamnal derivative, (iii) removal of protecting group and oxidation of the 2-hydroxy group, (iv) dihydroxylation of the pseudoglycal from the sterically more hindered side and finally (v) ring closure by acetal formation under acidic conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.028
• 作为产物：
  描述：

  薯蓣皂素 在 palladium on activated charcoal 氢气 、 二甲基二环氧乙烷 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， -30.0~20.0 ℃ 、200.0 kPa 条件下， 反应 53.08h， 生成 (25R)-2α-hydroxy-5α-spirostan-3-one
  参考文献：
  名称：

  Preparation of an analogue of orbicuside A, an unusual cardiac glycoside

  摘要：

  A steroid containing a multi-linked glycoside, analogous to the bufadienolide orbicuside A, has been prepared. The key steps were (i) the preparation of a 2alpha-allyloxycarbonyloxy-3beta-hydroxy steroid, (ii) a Ferrier reaction between the steroid and a rhamnal derivative, (iii) removal of protecting group and oxidation of the 2-hydroxy group, (iv) dihydroxylation of the pseudoglycal from the sterically more hindered side and finally (v) ring closure by acetal formation under acidic conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.028

文献信息

• Total synthesis and cytotoxicity evaluation of the spirostanol saponin gitonin
  作者：Yong Li、Xun Lv、Jun Liu、Yuguo Du

  DOI：10.1039/d3ob02101g

  日期：——

  commercially available isopropyl β-D-1-thiogalactopyranoside (IPTG) and tigogenin. A cascade two-step glycosylation and Schmidt's inverse procedure significantly facilitated the synthesis of gitonin and its derivatives. The cytotoxic activities of gitonin and its structural analogues were evaluated against A549, HepG2, and MCF-7, and most of them exhibited moderate to excellent inhibitory activity. Our study

  由市售的异丙基 β- D -1-硫代半乳糖苷 (IPTG) 和替高配元，通过 12 个步骤（最长的线性序列）有效合成了螺甾烷皂苷 gitonin，总产率为 18.5%。级联两步糖基化和施密特逆过程显着促进了 gtonin 及其衍生物的合成。对A549、HepG2和MCF-7的Gtonin及其结构类似物的细胞毒活性进行了评估，其中大多数表现出中等至优异的抑制活性。我们的研究表明，从 gitonin 中去除 β- D-吡喃半乳糖基残基（连接在葡萄糖单元的 C-2 处）不会降低抑制活性；然而，糖单元的进一步裂解可能会严重降低活性。对这些癌细胞系的生物测定还表明，苷元上 2α-羟基的存在削弱了设计的皂苷的细胞毒性。