5,6α-epoxy-5α-sitostan-3β-ol acetate | 131321-89-6

• 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: 5,6α-epoxy-5α-sitostan-3β-ol acetate
• 英文别名: 3β-acetoxy-5,6α-epoxystigmastane；acetic acid-(5,6α-epoxy-5α-stigmastan-3β-yl ester)；Essigsaeure-(5,6α-epoxy-5α-stigmastan-3β-ylester)；[(1S,2R,5S,7R,9S,11S,12S,15R,16R)-15-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-yl] acetate
• CAS: 131321-89-6
• 化学式: C₃₁H₅₂O₃
• 分子量: 472.752
• InChiKey: UZDSGVFJNPWYPD-MGAPJDORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6α-epoxy-5α-sitostan-3β-ol acetate 在 chromium(VI) oxide 作用下， 以 水 为溶剂， 生成 (24R)-3β,5-dihydroxy-5α-stigmastan-6-one-3-acetate
  参考文献：
  名称：

  Isolation and synthesis of the first natural 6-hydroximino 4-en-3-one- steroids from the sponges Cinachyrella spp

  摘要：

  Two new 6-hydroximino-4en-3-one steroids: (24R, 6E)-24-ethylcholest-6-hydroximino-4-en-3-one (1) and (6E) cholest-6-hydroximino-4-en-3-one (2), accompanied by the known cholest-4-en-3-one were isolated from a mixture of two morphospecies of the sponge Cinachyrella (C. alloclada and C. apion). Use of spectroscopic methods (NMR and MS) was key to establish their structures which were confirmed by synthesis. Described in this report are the fast hydroximino steroids derived from a natural source. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00163-9
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 5,6α-epoxy-5α-sitostan-3β-ol acetate
  参考文献：
  名称：

  SOUTH AFRICAN GEOMORPHOLOGY: CRITICAL CHOICES FOR THE FUTURE

  摘要：

  DOI：

  10.1080/03736245.2002.9713765

文献信息

• Synthesis of highly pure oxyphytosterols and (oxy)phytosterol estersPart I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols
  作者：Philippe Geoffroy、Diane Julien-David、Eric Marchioni、Francis Raul、Dalal Aoudé-Werner、Michel Miesch

  DOI：10.1016/j.steroids.2008.02.004

  日期：2008.8

  The synthesis of several oxyphytosterols is described starting from stigmasterol, the key step being the regioselective hydrogenation of the 22-23 double bond of the latter. (C) 2008 Elsevier Inc. All rights reserved.
• A concise synthesis of β-sitosterol and other phytosterols
  作者：Jiliang Hang、Patrick Dussault

  DOI：10.1016/j.steroids.2010.05.016

  日期：2010.12

  A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of beta-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Delta(22-23) phytosterols. (C) 2010 Elsevier Inc. All rights reserved.
• Shafiullah; Jamaluddin, Malik, Acta Chimica Hungarica, 1990, vol. 127, # 1, p. 83 - 86
  作者：Shafiullah、Jamaluddin, Malik

  DOI：——

  日期：——
• Gram-scale chromatographic purification of β-sitosterolSynthesis and characterization of β-sitosterol oxides
  作者：X ZHANG、P GEOFFROY、M MIESCH、D JULIENDAVID、F RAUL、D AOUDEWERNER、E MARCHIONI

  DOI：10.1016/j.steroids.2005.06.003

  日期：2005.12.1

  An effective purification method for P-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. P-Sitosterol (>= 95% purity) was obtained on a gram-scale. Thus, the synthesis of six P-sitosterol oxides, including 7 alpha-hydroxy, 7 beta-hydroxy, 5,6 alpha-epoxy, 5,6 beta-epoxy, 7-keto, and 5 alpha,6 beta-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (similar to 95% purity) were well-documented. (c) 2005 Elsevier Inc. All rights reserved.
• SHAFIULLAH;JAMALUDDIN, MALIK, ACTA CHIM. HUNG., 127,(1990) N, C. 83-86
  作者：SHAFIULLAH、JAMALUDDIN, MALIK

  DOI：——

  日期：——