(25ξ)-26-hydroxycholesteryl diacetate | 17367-15-6

• 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: (25ξ)-26-hydroxycholesteryl diacetate
• 英文别名: 5-cholestene-3β,27-diol diacetate；27-hydroxycholesterol diacetate；26-hydroxy-cholesterol-diacetate；26-Hydroxycholesterol diacetate；[(6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptyl] acetate
• CAS: 17367-15-6
• 化学式: C₃₁H₅₀O₄
• 分子量: 486.736
• InChiKey: BHIIFKXBBYKZCA-AFJNEFTNSA-N

物化性质

• 沸点：
  539.7±33.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (25ξ)-26-hydroxycholesteryl diacetate 在 lipase from Candida cylindracea 、 辛醇 作用下， 以 various solvent(s) 为溶剂， 反应 144.0h， 以90%的产率得到(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇
  参考文献：
  名称：

  类固醇酯在有机溶剂中的酶促酯交换反应

  摘要：

  描述了一种在有机溶剂中通过脂肪酶催化的酯交换反应将甾族酯转化为相应醇的温和方法。记录了反应的立体选择性和区域选择性的方面。

  DOI：

  10.1016/s0040-4039(00)96910-7
• 作为产物：
  描述：

  Kryptogenin 在 吡啶 、 盐酸 、 汞 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (25ξ)-26-hydroxycholesteryl diacetate
  参考文献：
  名称：

  Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs

  摘要：

  In connection with studies of alternative pathways in bile acid biosynthesis, potential intermediates in a pathway starting with 27-hydroxylation of cholesterol have been prepared in natural and deuterated forms. Established methods were used to prepare 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid. Clemmensen reduction of kryptogenin in unlabeled and deuterated solvents yielded 27-hydroxy-cholesterol and 16-oxo-5-cholestene-3beta,27-diol, which were separated by adsorption chromatography on Unisil. The labeled 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid derived from it consisted of molecules with seven (50%), six (20%), and eight (20%) deuterium atoms, and unlabeled molecules were not detected. The acetates of 27-hydroxycholesterol and methyl 3beta-hydroxy-5-cholestenoate were 7alpha-hydroxylated in a copper-catalyzed reaction with tert-butylperbenzoate, and the products were purified by chromatography on Unisil. The 7beta-epimers were obtained as side products. Labeled 3beta,7alpha-dihydroxy-5-cholenoic acid was prepared in the same way from 3beta-hydroxy-5-[2,2,4,4,23-H-2(5)-cholenoic acid. The 3-oxo-DELTA4 analogs of the 3beta-hydroxy-DELTA5 compounds were prepared by oxidation with cholesterol oxidase. The labeled products had the same isotopic composition as the starting materials. Gas chromatographic retention indices and mass spectral characteristics of the trimethylsilyl ether derivatives of the neutral steroid and the methylated acids are given for all compounds.

  DOI：

  10.1016/0039-128x(93)90048-r

文献信息

• Bile acids. LXVIII. Allylic and benzylic photo-chemical oxidation of steroids
  作者：Daniel M. Tal、William H. Elliott

  DOI：10.1016/0039-128x(83)90034-x

  日期：1983.5

  highly selective low energy UV lamp in the presence of mercuric bromide. With this procedure cholesterol acetate, 5-cholestene-3 beta, 27-diol diacetate, 24(R)-24-methyl-5-cholesten-2 beta-yl acetate, 24(R)-24-ethyl-5-cholesten-28-yl acetate and 24(R)-24-ethyl-(22E)-cholesta-5,22-dien-3 beta-yl acetate were oxidized to the allylic keto-derivative in good yields; estradiol-17 beta diacetate was similarly

  为了提供产率高于化学氧化获得的7-氧胆固醇的衍生物，研究了甾体烯丙基或苄基酮的制备。在溴化汞存在的情况下，使用高选择性低能量紫外灯研究了空气诱导的氧化。通过该程序，乙酸胆固醇，5-胆甾烯-3β，27-二醇二乙酸酯，24（R）-24-甲基-5-胆甾烯-2β-乙酸乙烯酯，24（R）-24-乙基-5-胆甾烯-将乙酸28-乙酸酯和24（R）-24-乙基-（22E）-胆甾-5,22-二烯-3β-乙酸乙酸酯氧化成烯丙基酮基衍生物，收率很高。类似地，雌二醇-17β二乙酸酯以提高的产率转化为6-氧代产物。该方法在合成乙酸7-氧胆固醇酯及其类似物和6-氧-雌甾烯中非常有用。
• NJAR, VINCENT C. O.;CASPI, ELIAHU, TETRAHEDRON LETT., 28,(1987) N 52, 6549-6552
  作者：NJAR, VINCENT C. O.、CASPI, ELIAHU

  DOI：——

  日期：——
• Enzymatic transesterification of steroid esters in organic solvents
  作者：Vincent C.O. Njar、Eliahu Caspi

  DOI：10.1016/s0040-4039(00)96910-7

  日期：——

  A mild procedure for the conversion of steroid esters into the corresponding alcohols via lipase-catalyzed transesterification reaction in organic solvents is described. Aspects of stereoselectivity and regioselectivity of the reaction are noted.

  描述了一种在有机溶剂中通过脂肪酶催化的酯交换反应将甾族酯转化为相应醇的温和方法。记录了反应的立体选择性和区域选择性的方面。
• Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs
  作者：Junichi Shoda、Magnus Axelson、Jan Sjövall

  DOI：10.1016/0039-128x(93)90048-r

  日期：1993.3

  In connection with studies of alternative pathways in bile acid biosynthesis, potential intermediates in a pathway starting with 27-hydroxylation of cholesterol have been prepared in natural and deuterated forms. Established methods were used to prepare 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid. Clemmensen reduction of kryptogenin in unlabeled and deuterated solvents yielded 27-hydroxy-cholesterol and 16-oxo-5-cholestene-3beta,27-diol, which were separated by adsorption chromatography on Unisil. The labeled 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid derived from it consisted of molecules with seven (50%), six (20%), and eight (20%) deuterium atoms, and unlabeled molecules were not detected. The acetates of 27-hydroxycholesterol and methyl 3beta-hydroxy-5-cholestenoate were 7alpha-hydroxylated in a copper-catalyzed reaction with tert-butylperbenzoate, and the products were purified by chromatography on Unisil. The 7beta-epimers were obtained as side products. Labeled 3beta,7alpha-dihydroxy-5-cholenoic acid was prepared in the same way from 3beta-hydroxy-5-[2,2,4,4,23-H-2(5)-cholenoic acid. The 3-oxo-DELTA4 analogs of the 3beta-hydroxy-DELTA5 compounds were prepared by oxidation with cholesterol oxidase. The labeled products had the same isotopic composition as the starting materials. Gas chromatographic retention indices and mass spectral characteristics of the trimethylsilyl ether derivatives of the neutral steroid and the methylated acids are given for all compounds.