4-[(6S,7S,8R,9S,13S,14S,17S)-6-(Imidazole-1-carbothioyloxy)-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 | 200722-01-6

• 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: 4-[(6S,7S,8R,9S,13S,14S,17S)-6-(Imidazole-1-carbothioyloxy)-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
• 英文别名: methyl 4-[(6S,7S,8R,9S,13S,14S,17S)-6-(imidazole-1-carbothioyloxy)-13-methyl-3,17-bis(2-trimethylsilylethoxymethoxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl]butanoate
• CAS: 200722-01-6
• 化学式: C₃₉H₆₂N₂O₇SSi₂
• 分子量: 759.167
• InChiKey: QMSRXZRLZHWLHC-SXPTWFNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.05
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[(6S,7S,8R,9S,13S,14S,17S)-6-(Imidazole-1-carbothioyloxy)-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 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以95%的产率得到3,17β-bis(2-trimethylsilyl)ethoxymethyl-7α-(3'-carbomethoxypropyl)estradiol
  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：

  (8R,9S,13S,14S,17S)-13-methyl-3,17-bis(2-trimethylsilylethoxymethoxy)-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-6-one 在 吡啶 、 六甲基磷酰三胺 、 sodium chlorite 、 sodium tetrahydroborate 、 2-甲基-2-丁烯 、 二甲基硫 、 sodium hexamethyldisilazane 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 31.5h， 生成 4-[(6S,7S,8R,9S,13S,14S,17S)-6-(Imidazole-1-carbothioyloxy)-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

文献信息

• A stereoselective synthesis of 7α-(3′-carboxypropyl)estradiol from a noncontrolled substance
  作者：Maciej Adamczyk、Donald D. Johnson、Rajarathnam E. Reddy

  DOI：10.1016/s0039-128x(97)00088-3

  日期：1997.12

  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.