Oestratrien-(1,3,5(10))-tetraol-(3,15α,16α,17β)-3,17-diacetat | 16127-99-4

• 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: Oestratrien-(1,3,5(10))-tetraol-(3,15α,16α,17β)-3,17-diacetat
• 英文别名: [(8R,9S,13S,14S,15R,16R,17R)-3-acetyloxy-15,16-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 16127-99-4
• 化学式: C₂₂H₂₈O₆
• 分子量: 388.461
• InChiKey: JCBSFUFZMPRJJS-ZEVCKCCMSA-N

物化性质

• 沸点：
  508.6±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Oestratrien-(1,3,5(10))-tetraol-(3,15α,16α,17β)-3,17-diacetat 在 无水碳酸镉 吡啶 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 3,16α,17β-triacetoxyestra-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：

  Oestratetraen-(1,3,5(10),15)-diol-(3,17β)-diacetat 在 四氧化锇 作用下， 以 吡啶 、 苯 为溶剂， 以12%的产率得到3,17β-diacetoxyestra-1,3,5(10)-triene-15β,16β-diol
  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

文献信息

• Process for the preparation of estetrol
  申请人：Pantarhei Bioscience B.V.

  公开号：EP2383279A1

  公开（公告）日：2011-11-02

  The present invention relates to a process for the preparation of estra-1,3,5(10)-trien-3,15α,16α,17β-tetraol (estetrol), via a silyl enol ether derivative 17-B-oxy-3-A-oxy-estra-1,3,5(10),16-tetraene, wherein A is a protecting group and B is ―Si(R2)3. The invention further relates to a process for the synthesis of 3-A-oxy-estra-1,3,5(10),15-tetraen-17-one, wherein A is a protecting group, via said silyl enol ether derivative.

  本发明涉及一种制备雌三醇（estetrol）的过程，通过使用硅烯醇醚衍生物17-B-氧-3-A-氧-雌三烯-1,3,5(10),16-四烯，其中A是保护基，B是―Si(R2)3。该发明还涉及一种合成3-A-氧-雌三烯-1,3,5(10),15-四烯-17-酮的过程，其中A是保护基，通过上述硅烯醇醚衍生物。
• Synthesis of estetrol via estrone derived steroids
  申请人：Verhaar Theodoor Mark

  公开号：US20060211669A1

  公开（公告）日：2006-09-21

  A process is provided for the making of estetrol starting from a 3-A-oxy-estra 1,3,5(10),15-tetraen-17-one, wherein A is a C 1 -C 5 alkyl group, preferably a methyl group, or a C 7 -C 12 benzylic group, preferably a benzyl group. This process is particularly suitable to industry.

  提供了一种制备雌四醇的过程，该过程从3-A-氧基-雌甾-1,3,5（10），15-四烯-17-酮开始，其中A是C1-C5烷基，优选为甲基，或C7-C12苄基，优选为苄基。该过程特别适用于工业。
• SYNTHESIS OF ESTETROL VIA ESTRONE DERIVED STEROIDS
  申请人：Pantarhei Bioscience B.V.

  公开号：US20150105362A1

  公开（公告）日：2015-04-16

  A process is provided for the making of estetrol starting from a 3-A-oxy-estra-1,3,5(10),15-tetraen-17-one, wherein A is an C 1 -C 5 alkyl group, preferably a methyl group, or a C 7 -C 12 benzylic group, preferably a benzyl group. This process is particularly suitable to industry.

  提供一种从3-A-氧基-雌甾-1,3,5（10），15-四烯-17-酮开始制备雌三醇的方法，其中A是C1-C5烷基，优选为甲基，或C7-C12苄基，优选为苄基。该方法特别适用于工业生产。
• PROCESS FOR THE PREPARATION OF ESTETROL
  申请人：Donesta Bioscience B.V.

  公开号：EP2734536B1

  公开（公告）日：2016-09-28
• INDUSTRIAL PROCESS FOR THE PREPARATION OF HIGH PURITY ESTETROL
  申请人：Richter Gedeon Nyrt.

  公开号：EP3877395B1

  公开（公告）日：2022-12-07