3,17β-bis(tert-butyldimethylsilyloxy)-estra-1,3,5(10)-trien-15α-ol | 58699-18-6

• 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: 3,17β-bis(tert-butyldimethylsilyloxy)-estra-1,3,5(10)-trien-15α-ol
• CAS: 58699-18-6
• 化学式: C₃₀H₅₂O₃Si₂
• 分子量: 516.912
• InChiKey: OEVBPYFYKPPIGK-KWKXJEFWSA-N

物化性质

• 沸点：
  524.3±50.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,17β-bis(tert-butyldimethylsilyloxy)-estra-1,3,5(10)-trien-15α-ol 在 无水碳酸镉 盐酸 、 jones reagent 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 72.58h， 生成 3-hydroxy-17-oxoestra-1,3,5(10)-trien-15α-yl-2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 15α-hydroxyestrogen 15-N-acetylglucosaminides

  摘要：

  The synthesis of 15-N-acetylglucosaminides of 15 alpha-hydroxyestrone, 15 alpha-hydroxyestradiol, and 15 alpha-hydroxyestriol (estetrol) is described. The latter two were prepared by condensation of 2-acetamido-1 alpha-chloro-1,2-dideoxy-3,4,6-trio-O-acetyl-D-glucopyranose with appropriately protected 15 alpha-hydroxyestrogens by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst. Subsequent removal of protecting groups with methanolic potassium hydroxide provided the desired conjugates. 15 alpha-Hydroxyestrone 15-N-acetylglucosaminide was synthesized from the corresponding 15 alpha-hydroxyestradiol derivative by Jones oxidation followed by brief alkaline hydrolysis. These conjugates underwent enzymatic hydrolysis with beta-N-acetylglucosaminidase from Jack beans to produce 15 alpha-hydroxyestrogens.

  DOI：

  10.1016/0039-128x(94)00054-g
• 作为产物：
  描述：

  estra-1,3,5(10),15-tetraene-3,17β-diol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,17β-bis(tert-butyldimethylsilyloxy)-estra-1,3,5(10)-trien-15α-ol
  参考文献：
  名称：

  Syntheses of 15α-Hydroxyestrone and 15α-Hydroxyestradiol

  摘要：

  通过新的合成路线，我们从雌酮中制备出了标题化合物（1、2）。用二硼烷对 14、15 或 15、16-双键进行氢硼化合，然后用碱性过氧化氢对有机硼烷进行氧化，很容易在 15α 位上引入羟基。在制备 1 的过程中，为了保护 3、17β-羟基，方便地使用了二甲基叔丁基硅烷官能团。

  DOI：

  10.1248/cpb.23.3141

文献信息

• Preparation of specific antisera to 15α-hydroxyestrogens
  作者：Emako Suzuki、Madoka Nakagomi、Mitsunori Hashimoto、Manabu Agui、Sayaka Iida、Kazunori Konno、Yasuo Hara、Hiroyuki Kurihara、Yasuhiko Matsuki、Kiyoshi Imai、Hiroshi Ono

  DOI：10.1016/s0039-128x(99)00031-8

  日期：1999.8

  The synthesis of haptens of 15 alpha-hydroxyestrone, 15 alpha-hydroxyestradiol, and 15 alpha-hydroxyestriol (estetrol) was undertaken, to obtain specific antisera required for enzyme immunoassay. 3-(1-Carboxypropyl) ethers of these 15 alpha-hydroxyestrogens were prepared and conjugated with bovine serum albumin and horseradish peroxidase. The specificity of antisera elicited against bovine serum albumin conjugates was checked by the enzyme immunoassay by using horseradish peroxidase-labeled antigen, and proved to be satisfactory in terms of cross-reactivities to related compounds. (C) 1999 Elsevier Science Inc. All rights reserved.