3β-(tert-butyldimethylsilyloxy)-20(S)-(2-dimethylaminocarbonylethyloxy)pregn-5-ene | 152397-56-3

• 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: 3β-(tert-butyldimethylsilyloxy)-20(S)-(2-dimethylaminocarbonylethyloxy)pregn-5-ene
• 英文别名: 3β-(t-butyldimethylsilyloxy)-20S-{2-(dimethylaminocarbonyl)ethyloxy}-5-pregnene；3-[(1S)-1-[(3S,8S,9S,10R,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethoxy]-N,N-dimethylpropanamide
• CAS: 152397-56-3
• 化学式: C₃₂H₅₇NO₃Si
• 分子量: 531.895
• InChiKey: HMRFINDLMOOFRT-QUYUTZPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-(tert-butyldimethylsilyloxy)-20(S)-(2-dimethylaminocarbonylethyloxy)pregn-5-ene 在 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 偶氮二异丁腈 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.25h， 生成 (3S,20S)-20-(3-hydroxy-3-methylbutoxy)pregna-5,7-dien-3-ol
  参考文献：
  名称：

  Synthesis of 1-Deoxymaxacalcitol

  摘要：

  1-Deoxymaxacalcitol, the 1-deoxygenated derivative of maxacalcitol practically used for the treatment of secondary hyperparathyroidism and psoriasis, has been synthesized for the biological evaluation. Although purification of the key intermediate containing 1,3-cyclohexadiene moiety was extremely difficult owing to inseparable contaminants, treatment of the mixture with the heterocyclic dienophile 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) formed the readily separable Diels-Alder adduct from which the target 1-deoxymaxacalcitol could be obtained in a pure state.

  DOI：

  10.3987/com-05-10463
• 作为产物：
  描述：

  (3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one 在 9-borabicyclo[3.3.1]nonane dimer 、 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 3β-(tert-butyldimethylsilyloxy)-20(S)-(2-dimethylaminocarbonylethyloxy)pregn-5-ene
  参考文献：
  名称：

  Synthesis of 1-Deoxymaxacalcitol

  摘要：

  1-Deoxymaxacalcitol, the 1-deoxygenated derivative of maxacalcitol practically used for the treatment of secondary hyperparathyroidism and psoriasis, has been synthesized for the biological evaluation. Although purification of the key intermediate containing 1,3-cyclohexadiene moiety was extremely difficult owing to inseparable contaminants, treatment of the mixture with the heterocyclic dienophile 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) formed the readily separable Diels-Alder adduct from which the target 1-deoxymaxacalcitol could be obtained in a pure state.

  DOI：

  10.3987/com-05-10463

文献信息

• Synthesis of tritiated 1α,25-dihydroxy-22-oxavitamin D3
  作者：Hiroyoshi Watanabe、Masashi Akiyama、Takehiko Kawanishi、Noboru Kubodera

  DOI：10.1002/jlcr.2580360706

  日期：1995.7

  Synthesis of two tritiated 1α,25-dihydroxy-22-oxavitamin D3 (OCT), [26-3H3]OCT (3) and [2β-3H]OCT (4), is described. [26-3H3]OCT (3) was prepared by tritiation at the side chain with tritiated methylmagnesium iodide and [2β-3H]OCT (4) was labeled at the A-ring by tritiation with sodium borotritiide.

  描述了两种氚标记的1α,25-二羟基-22-氧维生素D3（OCT），即[26-3H3]OCT (3)和[2β-3H]OCT (4)的合成。[26-3H3]OCT (3)是通过用氚标记的甲基镁碘化物对侧链进行氚标记而制备的，而[2β-3H]OCT (4)则是通过与硼氚化钠进行氚标记在A环上标记的。
• 22-oxacholecalciferol derivative and process for preparing the same
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US05436401A1

  公开（公告）日：1995-07-25

  A 22-oxacholecalciferol derivative represented by formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom or a hydroxyl group; and R.sub.2 and R.sub.3, which may be the same or different, each represent a lower alkyl group having from 1 to 5 carbon atoms, and a process for preparing the same are disclosed. The compound of the present invention has potent differentiation inducing activity and cell proliferation inhibitory activity and is expected to be useful as an anti-tumor agent, an antirheumatic, a treating agent for psoriasis, and a treating agent for hyperparathyreosis. The process of the present invention makes it possible to efficiently produce a desired 22-oxacholecalciferol derivative while reducing by-production.

  本发明公开了一种由公式（I）表示的22-氧合胆钙化醇衍生物：##STR1## 其中R.sub.1代表氢原子或羟基；R.sub.2和R.sub.3，可以相同也可以不同，每个代表具有1至5个碳原子的较低烷基基团，以及制备该衍生物的方法。本发明化合物具有强烈的诱导分化活性和细胞增殖抑制活性，预计可用作抗肿瘤剂、抗风湿剂、治疗牛皮癣的治疗剂和治疗甲状旁腺功能亢进的治疗剂。本发明的方法使得可以高效地生产所需的22-氧合胆钙化醇衍生物，同时减少副产物的产生。
• Synthesis of 1-Deoxymaxacalcitol
  作者：Tsuyoshi Yamauchi、Masahiro Kato、Tetsuhiro Mikami、Yasuo Fujimura

  DOI：10.3987/com-05-10463

  日期：——

  1-Deoxymaxacalcitol, the 1-deoxygenated derivative of maxacalcitol practically used for the treatment of secondary hyperparathyroidism and psoriasis, has been synthesized for the biological evaluation. Although purification of the key intermediate containing 1,3-cyclohexadiene moiety was extremely difficult owing to inseparable contaminants, treatment of the mixture with the heterocyclic dienophile 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) formed the readily separable Diels-Alder adduct from which the target 1-deoxymaxacalcitol could be obtained in a pure state.