3,17β-bis(2-trimethylsilyl)ethoxymethyl-7α-(3'-carbomethoxypropyl)estradiol | 200722-03-8

• 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: 3,17β-bis(2-trimethylsilyl)ethoxymethyl-7α-(3'-carbomethoxypropyl)estradiol
• CAS: 200722-03-8
• 化学式: C₃₅H₆₀O₆Si₂
• 分子量: 633.029
• InChiKey: VNWTYTXNEIIEEO-DKQMVKHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  43.0
• 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：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,17β-bis(2-trimethylsilyl)ethoxymethyl-7α-(3'-carbomethoxypropyl)estradiol 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 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：

  (7S,8R,9S,13S,14S,17S)-13-Methyl-7-pent-4-enyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-6-one 在 吡啶 、 sodium chlorite 、 sodium tetrahydroborate 、 2-甲基-2-丁烯 、 二甲基硫 、 偶氮二异丁腈 、 三正丁基氢锡 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙酸乙酯 、 甲苯 、 叔丁醇 为溶剂， 反应 18.0h， 生成 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

文献信息

• Evaluation of chemiluminescent estradiol conjugates by using a surface plasmon resonance detector
  作者：Maciej Adamczyk、Yon-Yih Chen、John C Gebler、Donald D Johnson、Phillip G Mattingly、Jeffrey A Moore、Rajarathnam E Reddy、Jiang Wu、Zhiguang Yu

  DOI：10.1016/s0039-128x(00)00091-x

  日期：2000.6

  A series of chemiluminescent 17 beta-estradiol probes were synthesized. Relative equilibrium dissociation constants (K-D) for the interaction of an anti-E-2 Fab fragment for the probes in solution were evaluated using a single E-2-analog biosensor surface on a BIAcore surface plasmon resonance instrument. The results show the antibody fragment binds all chemiluminescent conjugates tested with high affinity showing only minor preferences for site of substitution (C6 versus C7), stereochemistry (alpha versus beta), or linker moiety. (C) 2000 Elsevier Science Inc. All rights reserved.