3β-acetoxy-12β-benzoyloxy-5α-furostan-26-ol | 404574-36-3

• 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: 3β-acetoxy-12β-benzoyloxy-5α-furostan-26-ol
• CAS: 404574-36-3
• 化学式: C₃₆H₅₂O₆
• 分子量: 580.805
• InChiKey: BEZPSHFNILLEJU-GOPJQFMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-12β-benzoyloxy-5α-furostan-26-ol 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3β-acetoxy-12β-benzoyloxy-5α-furostan-26-azide
  参考文献：
  名称：

  Discovery of Hypoiodite-Mediated Aminyl Radical Cyclization Lacking a Nitrogen Radical-Stabilizing Group: Application to Synthesis of an Oxazaspiroketal-Containing Cephalostatin Analog

  摘要：

  Synthesis of an oxazaspiroketal-containing bissteroidal pyrazine is described. The key transformation of this synthesis involves stereoselective formation of oxazaspiroketal via aminyl-radical cyclization of primary amine lacking a radical-stabilizing group by Suarez hypoiodite oxidation.

  DOI：

  10.1021/ol2017033
• 作为产物：
  描述：

  苯甲酰氯 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 3β-acetoxy-12β-benzoyloxy-5α-furostan-26-ol
  参考文献：
  名称：

  Discovery of Hypoiodite-Mediated Aminyl Radical Cyclization Lacking a Nitrogen Radical-Stabilizing Group: Application to Synthesis of an Oxazaspiroketal-Containing Cephalostatin Analog

  摘要：

  Synthesis of an oxazaspiroketal-containing bissteroidal pyrazine is described. The key transformation of this synthesis involves stereoselective formation of oxazaspiroketal via aminyl-radical cyclization of primary amine lacking a radical-stabilizing group by Suarez hypoiodite oxidation.

  DOI：

  10.1021/ol2017033

文献信息

• Mild Isomerative Opening of Tetrahydrofuranyl Subunits in Steroids Using TFAT (trifluoroacetyl trifluoromethanesulfonate): Application to Synthesis of C17-OH Rockogenin Acetate
  作者：Jong-Seok Lee、Byung-Sook Kim、Jun-Ho Shin、Yeon-Ju Lee、Hee-Jae Shin、Hyi-Seung Lee

  DOI：10.5012/bkcs.2012.33.1.76

  日期：2012.1.20

  A novel and efficient tetrahydrofuranyl ring opening method was developed using the highly reactive TFAT reagent in the presence of an acid scavenger, 2,6-di-tert-butyl-4-methylpyridine. Various acid sensitive groups are compatible with the reaction condition, making it generally applicable to many tetrahydrofuranyl steroids. Moreover, it is a synthetic equivalent of 'Marker degradation' affording an efficient synthesis of C17-OH rockogenin acetate.

  在酸清除剂 2,6-二叔丁基-4-甲基吡啶的存在下，利用高活性 TFAT 试剂开发了一种新型高效的四氢呋喃基开环方法。该反应条件与各种酸敏感基团兼容，因此普遍适用于多种四氢呋喃类固醇。此外，它还是 "标记降解 "的合成等价物，可高效合成 C17-OH 冰片甙元醋酸酯。
• Redox Refunctionalization of Steroid Spiroketals. Structure Correction of Ritterazine M
  作者：Seongmin Lee、Thomas G. LaCour、Douglas Lantrip、Philip L. Fuchs

  DOI：10.1021/ol0165894

  日期：2002.2.1

  The structure of the North spiroketal moiety of ritterazine M has been corrected from 1a to 1b. This was accomplished by comparison of published spectra of the natural product with five synthetic spiroketal-alcohols. Synthesis of these models was efficiently accomplished by reductive cleavage of the spiroketal and Sharpless asymmetric dihydroxylation of an isopentyl, methyl 1,1-disubstituted olefin

  利他嗪M的北部螺环结构的结构已从1a修正为1b。这是通过比较已公开的天然产物光谱与五种合成螺酮醇来完成的。这些模型的合成是通过以下方法有效地完成的：首先对异戊基甲基1,1-二取代的烯烃进行螺环的还原裂解和Sharpless不对称二羟基化反应，然后对Suarez碘[III]进行单保护的1度，3度1,2二醇的氧化螺环化反应。
• An Efficient C−H Oxidation Protocol for α-Hydroxylation of Cyclic Steroidal Ethers
  作者：Seongmin Lee、Philip L. Fuchs

  DOI：10.1021/ol049712a

  日期：2004.4.1

  Various C-16 hydroxy steroids have been prepared with the aid of CrO3/Bu4NIO4. Out of the two possible reaction courses, transition state B is favored because of less steric interference between substrate and CrO4. Thus, C-H bonds at C-16 are oxidized selectively.