[(3S,8R,9S,10R,13S,14S,17S)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] octanoate | 191677-78-8

• 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: [(3S,8R,9S,10R,13S,14S,17S)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] octanoate
• CAS: 191677-78-8
• 化学式: C₄₃H₆₂O₃Si
• 分子量: 655.049
• InChiKey: DIKPKFBNWNRZEZ-PVDIMVIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.17
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3S,8R,9S,10R,13S,14S,17S)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] octanoate 在 3,5-二甲基吡唑 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以44%的产率得到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
  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：

  叔丁基二苯基氯硅烷 在 吡啶 、 咪唑 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 140.5h， 生成 [(3S,8R,9S,10R,13S,14S,17S)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] octanoate
  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

• A direct stereoselective synthesis of 7β-hydroxytestosterone
  作者：David Labaree、Robert M. Hoyte、Richard B. Hochberg

  DOI：10.1016/s0039-128x(97)00018-4

  日期：1997.6

  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.