[(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-acetic acid methyl ester | 58699-52-8

• 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,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-acetic acid methyl ester
• CAS: 58699-52-8
• 化学式: C₂₇H₄₂O₄
• 分子量: 430.628
• InChiKey: YGJRTSLLLFDCLP-BRJORGASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-acetic acid methyl ester 在 碘 、 lithium methanethiolate 、 碳酸氢钠 、 sodium carbonate 、 lithium cyclohexylisopropylamide 、 potassium iodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 22.5h， 生成 (R)-4-((R)-3,3-Dimethyl-oxiranyl)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butyric acid methyl ester
  参考文献：
  名称：

  24(R), 25-Dihydroxycholesterol; An Attempt for Side-Chain Stereocontrol Via Iodolactonization

  摘要：

  AbstractStereocontrolled formation of the side‐chain of 24(R), 25‐dihydroxycholesterol (1) via an iodolactonization process, involving a C‐10 carboxylic function and a 24, 25 double bond, has been studied. Low stereoselectivity was observed.

  DOI：

  10.1002/bscb.19860950410
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 Methyl 3β-hydroxypregn-5-en-21-oate 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 [(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of 26,27-bisnorcastasterone analogs and analysis of conformation–activity relationship for brassinolide-like activity

  摘要：

  Three castasterone (CS) derivatives with varied side-chain moieties, 26,27-bisnorcastasterone (20S-bisilorCS), 20-epi-26,27-bisnorcastastcrone (20R-bisnorCS), and 21,26,27-trisnorcastasterone (trisnorCS), were synthesized stereoselectively from either stigmasterol or dehydroisoandrosterone. The 50% effective doses (ED50, nmol/plant) in the concentration-response Curve for brassinolide-like activity in the rice lamina inclination assay were determined to be 0.020 nmol (pED(50) = 10.7) for 20S-bisnorCS, 3.2 nmol (pED50 = 8.5) for 20R-bisnorCS, and 2.0 nmol (pED50 = 8.7) for trisnorCS. An analog containing an ester linkage between the steroid and the side-chain moiety of 20S-bisnorCS was also synthesized and its activity was evaluated to be 3.2 nmol (pED50 = 8.5), being equipotent to 20R-bisnorCS and trisnorCS. The activity of 20S-bisnorCS was 1/40 that of CS. The conformation analysis was conducted using a systematic search, showing that the activity decreases with an increase in the degree of freedom of the side chain of the steroidal skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.024

文献信息

• Use of malonic acid derivatives for the construction of substituted side chains in the position 17β of steroids
  作者：Pavel Drašar、Vladimír Pouzar、Ivan Černý、Miroslav Havel、Sofia N. Ananchenko、Igor V. Torgov

  DOI：10.1135/cccc19821240

  日期：——

  Using the Knoevenagel reaction condensation products of 3β-acetoxyandrost-5-en-17-one with diethyl malonate, ethyl cyanoacetate and malononitrile were prepared which converted to derivatives of 3β-hydroxypregn-5-en-21-oic acid. Reductions and oxidations of the double bonds in the positions 5,6 and 17,20 and the stereochemistry at atoms C₍₁₇₎ and C₍₂₀₎ of some derivatives were also investigated. From derivatives of 23,24-dinorchola-5,17(20)-diene-21,22-diol compounds with a 1,3-dioxane ring in the side chain were prepared.

  使用Knoevenagel反应对3β-乙酰氧基雄烯-5-烯-17-酮与二乙基丙二酸酯、氰乙酸乙酯和丙二腈进行缩合反应，制备了3β-羟基孕酮-5-烯-21-酸衍生物。还研究了一些衍生物中5、6和17、20位置的双键的还原和氧化，以及C₍₁₇₎和C₍₂₀₎原子的立体化学。从23,24-二去甲胆甾-5,17(20)-二烯-21,22-二醇衍生物中制备了侧链中含有1,3-二氧杂环的化合物。