Octanoic acid (7S,8R,9S,10R,13S,14S,17S)-7-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester | 191677-98-2

• 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: Octanoic acid (7S,8R,9S,10R,13S,14S,17S)-7-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
• 英文别名: [(7S,8R,9S,10R,13S,14S,17S)-7-hydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] octanoate
• CAS: 191677-98-2
• 化学式: C₂₇H₄₂O₄
• 分子量: 430.628
• InChiKey: CMARBEBXJBXXBB-RBNQBTAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Octanoic acid (7S,8R,9S,10R,13S,14S,17S)-7-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 在 hydroxypropyl β-cyclodextrin 、 phosphate buffer 、 porcine lipase 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以75%的产率得到7β,17β-dihydroxyandrost-4-ene-3-one
  参考文献：
  名称：

  A direct stereoselective synthesis of 7β-hydroxytestosterone

  摘要：

  Although 7 beta-hydroxytestosterone is a known product androgen metabolism, there are no published methods for its chemical synthesis except from the equally difficult to obtain 7 beta-hydroxy-4-androstene-3,17-dione. We found that several seemingly straightforward routes for its synthesis failed. Consequently, we tried to produce 7 beta-hydroxytestosterone by enzymatic oxidation of 5-androstene-3 beta,7 beta,17 beta-triol with cholesterol oxidase (Brevibacterium sp.), a procedure previously used to synthesize 7 beta-hydroxy-4-cholesten-3-one from 3 beta,7 beta-dihydroxycholesterol (Alexander and Fisher 1995). However, 5-androstene-3 beta,7 beta,17 beta-triol was, at best, a very poor substrate for the enzyme leading to the production of 7 beta-hydroxytestosterone in only trace amounts. Thus, we explored a strategy for the enzymatic synthesis in which a C-8-ester at C-17 (5-androstene-3 beta,7 beta,17 beta-triol 17-caprylate) would serve to mimic the bulky and hydrophobic side chain of cholesterol and thus allow the C-19-steroid to act as an effective substrate. When this ester was incubated with cholesterol oxidase, it was converted efficiently to 7 beta-hydroxytestosterone-17-caprylate. Attempts to remove the ester group by several mild hydrolytic procedures caused elimination of the 7 beta-hydroxyl group; we, therefore, obtained 7 beta-hydroxy-testosterone by incubation of the intermediate ester with porcine lipase. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00018-4
• 作为产物：
  描述：

  Octanoic acid (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 在 hydroxypropyl β-cyclodextrin 、 sodium tetrahydroborate 、 phosphate buffer 、 cerium(III) chloride 、 cholesterol oxidase from Brevibacterium sp 、 四丁基氟化铵 、 catalase from bovine liver 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 134.0h， 生成 Octanoic acid (7S,8R,9S,10R,13S,14S,17S)-7-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
  参考文献：
  名称：

  A direct stereoselective synthesis of 7β-hydroxytestosterone

  摘要：

  Although 7 beta-hydroxytestosterone is a known product androgen metabolism, there are no published methods for its chemical synthesis except from the equally difficult to obtain 7 beta-hydroxy-4-androstene-3,17-dione. We found that several seemingly straightforward routes for its synthesis failed. Consequently, we tried to produce 7 beta-hydroxytestosterone by enzymatic oxidation of 5-androstene-3 beta,7 beta,17 beta-triol with cholesterol oxidase (Brevibacterium sp.), a procedure previously used to synthesize 7 beta-hydroxy-4-cholesten-3-one from 3 beta,7 beta-dihydroxycholesterol (Alexander and Fisher 1995). However, 5-androstene-3 beta,7 beta,17 beta-triol was, at best, a very poor substrate for the enzyme leading to the production of 7 beta-hydroxytestosterone in only trace amounts. Thus, we explored a strategy for the enzymatic synthesis in which a C-8-ester at C-17 (5-androstene-3 beta,7 beta,17 beta-triol 17-caprylate) would serve to mimic the bulky and hydrophobic side chain of cholesterol and thus allow the C-19-steroid to act as an effective substrate. When this ester was incubated with cholesterol oxidase, it was converted efficiently to 7 beta-hydroxytestosterone-17-caprylate. Attempts to remove the ester group by several mild hydrolytic procedures caused elimination of the 7 beta-hydroxyl group; we, therefore, obtained 7 beta-hydroxy-testosterone by incubation of the intermediate ester with porcine lipase. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00018-4

文献信息

• NEW ENZYMATIC PROCESS FOR THE PREPARATION OF TESTOSTERONE AND ESTERS THEREOF
  申请人：F.I.S.- FABBRICA ITALIANA SINTETICI S.P.A

  公开号：US20170029863A1

  公开（公告）日：2017-02-02

  The present invention relates to a new process for the preparation of testosterone by means of enzymatic hydrolysis of testosterone esters.

  本发明涉及一种通过酶解睾酮酯类物质制备睾酮的新工艺。
• ENZYMATIC PROCESS FOR THE PREPARATION OF TESTOSTERONE AND ESTERS THEREOF
  申请人：F.I.S.- Fabbrica Italiana Sintetici S.p.A.

  公开号：EP3124616A1

  公开（公告）日：2017-02-01

  The present invention relates to a new process for the preparation of testosterone by means of enzymatic hydrolysis of testosterone esters, wherein the enzyme is a lipase from Humicola insolens or a lipase from Candida antarctica A.

  本发明涉及一种通过酶水解睾酮酯制备睾酮的新工艺，其中的酶是来自 Humicola insolens 的脂肪酶或来自 Candida antarctica A 的脂肪酶。
• US9970042B2
  申请人：——

  公开号：US9970042B2

  公开（公告）日：2018-05-15