(25R)-2α-allyloxycarbonyloxy-5α-spirostan-3β-ol | 848854-29-5

• 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-allyloxycarbonyloxy-5α-spirostan-3β-ol
• CAS: 848854-29-5
• 化学式: C₃₁H₄₈O₆
• 分子量: 516.719
• InChiKey: ZEWVIXLUBGKOQQ-YJIGILJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  37.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (25R)-2α-allyloxycarbonyloxy-5α-spirostan-3β-ol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,2-双(二苯基膦)乙烷 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 水 、 戴斯-马丁氧化剂 、 环氧氯丙烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 33.08h， 生成 (25R)-3β-(4'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-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 吡啶 、 sodium tetrahydroborate 、 氢气 、 二甲基二环氧乙烷 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， -40.0~20.0 ℃ 、200.0 kPa 条件下， 反应 55.58h， 生成 (25R)-2α-allyloxycarbonyloxy-5α-spirostan-3β-ol
  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

• Preparation of an analogue of orbicuside A, an unusual cardiac glycoside
  作者：John T. Dixon、Fanie R. van Heerden、Cedric W. Holzapfel

  DOI：10.1016/j.tetasy.2004.11.028

  日期：2005.1

  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.