4-[(6S,7S,8R,9S,13S,14S,17S)-6-Hydroxy-13-methyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-butyric acid methyl ester | 200721-99-9

• 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: 4-[(6S,7S,8R,9S,13S,14S,17S)-6-Hydroxy-13-methyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-butyric acid methyl ester
• CAS: 200721-99-9
• 化学式: C₃₅H₆₀O₇Si₂
• 分子量: 649.028
• InChiKey: DXSZGCHREFLKLR-ZXBOBGJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[(6S,7S,8R,9S,13S,14S,17S)-6-Hydroxy-13-methyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-butyric acid methyl ester 在 偶氮二异丁腈 、 氢氟酸 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 14.0h， 生成 4-((7R,8R,9S,13S,14S,17S)-3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl)-butyric acid methyl ester
  参考文献：
  名称：

  A stereoselective synthesis of 7α-(3′-carboxypropyl)estradiol from a noncontrolled substance

  摘要：

  Alkylation of 3,17 beta-bis(2-trimethylsilyl)ethoxymethyl-1,3,5(10) estratriene-6-one (2) with 5-bromo-1-pentene using NaHMDS in THF afforded 3,17 beta-bis(2-trimethylsilyl)ethoxymethyl-7-alpha-(4'-pentenyl)-1,3,5(10)estratriene-6-one (3) in excellent stereoselectivity (>95% epimeric excess. Functionalization of the side chain in compound 3 was accomplished via ozonolysis, oxidation and esterification to give 5 in 72% yield. The reduction of ester (5) using NaBH4 in MeOH afforded the corresponding 6 alpha-hydroxy compound (6) as a single isomer in 72% yield. The hydroxyl group in 6 was removed by converting to the corresponding xanthate (7) followed by reduction using n-Bu3SnH to afford 8 in good yield. Finally, the SEM protective groups in 8 were removed, after which the ester function was hydrolyzed with LiOH to give 7 alpha-(3'-carboxypropyl)estradiol (10), in 10.6% overall yield from 3. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00088-3
• 作为产物：
  描述：

  4-[(7S,8R,9S,13S,14S,17S)-13-Methyl-6-oxo-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-butyric acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以70%的产率得到4-[(6S,7S,8R,9S,13S,14S,17S)-6-Hydroxy-13-methyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-butyric acid methyl ester
  参考文献：
  名称：

  A stereoselective synthesis of 7α-(3′-carboxypropyl)estradiol from a noncontrolled substance

  摘要：

  Alkylation of 3,17 beta-bis(2-trimethylsilyl)ethoxymethyl-1,3,5(10) estratriene-6-one (2) with 5-bromo-1-pentene using NaHMDS in THF afforded 3,17 beta-bis(2-trimethylsilyl)ethoxymethyl-7-alpha-(4'-pentenyl)-1,3,5(10)estratriene-6-one (3) in excellent stereoselectivity (>95% epimeric excess. Functionalization of the side chain in compound 3 was accomplished via ozonolysis, oxidation and esterification to give 5 in 72% yield. The reduction of ester (5) using NaBH4 in MeOH afforded the corresponding 6 alpha-hydroxy compound (6) as a single isomer in 72% yield. The hydroxyl group in 6 was removed by converting to the corresponding xanthate (7) followed by reduction using n-Bu3SnH to afford 8 in good yield. Finally, the SEM protective groups in 8 were removed, after which the ester function was hydrolyzed with LiOH to give 7 alpha-(3'-carboxypropyl)estradiol (10), in 10.6% overall yield from 3. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00088-3