20-(3-羟基-3-甲基丁氧基)孕甾-5,7-二烯-1,3-二醇 | 142785-61-3

• 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
• 中文名称: 20-(3-羟基-3-甲基丁氧基)孕甾-5,7-二烯-1,3-二醇
• 中文别名: 3-氨基-5-C-(3-羧基-4-(羧基甲基)-2-羰基-3-环己烯-1-基)呋喃阿卓糖
• 英文名称: 1α,3β-dihydroxy-20(S)-(3-hydroxy-3-methylbutyloxy)pregna-5,7-diene
• 英文别名: 20(S)-(3-hydroxy-3-methylbutyloxy)-pregna-5,7-diene-1α,3β-diol；(1S,3R,20S)-20-(3-hydroxy-3-methylbuthyloxy)pregna-5,7-dien-1,3-diol；22-oxacholesta-5,7-diene-1α,3β,25-triol；1α,3β-Dihydroxy-20S-(3-hydroxy-3-methylbutyloxy)pregna-5,7-diene；1α,3β-dihydroxy-20S-(3-methyl-3-hydroxybutyloxy)-5,7-pregnadiene；(1S,3R,20S)-20-(3-hydroxy-3-methylbutoxy)pregna-5,7-diene-1,3-diol；Hmbop；(1S,3R,9S,10R,13S,14R,17S)-17-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-1,3-diol
• CAS: 142785-61-3
• 化学式: C₂₆H₄₂O₄
• 分子量: 418.617
• InChiKey: DUZLDPYKMSNPLT-PUXWAVTRSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  580.2±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  20-(3-羟基-3-甲基丁氧基)孕甾-5,7-二烯-1,3-二醇 在 2-二甲氨基吡啶 、 乙酸酐 作用下， 以 吡啶 、 水 为溶剂， 以89%的产率得到1α,3β-diacetyloxy-20S-(3-hydroxy-3-methylbutyloxy)pregna-5,7-diene
  参考文献：
  名称：

  Highly crystalline 22-oxavitamin D derivatives

  摘要：

  高结晶维生素D衍生物的化学式为：##STR1##（其中R.sub.1是直链或支链的C.sub.4-C.sub.9烷基，可选地带有一个羟基；R.sub.2和R.sub.3可能相同或不同，均为酰基），通过水解上述化合物得到高纯度的22-氧化维生素D衍生物，该衍生物可用作药物。

  公开号：

  US05726330A1
• 作为产物：
  描述：

  (1S,3R)-bis(tert-butyldimethylsiloxy)-(20S)-2-tetrahydropyranoxyandrost-5-en 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 三氟化硼乙醚 、 四丁基氟化铵 、 双氧水 、 sodium hydride 、 乙硫醇 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 20-(3-羟基-3-甲基丁氧基)孕甾-5,7-二烯-1,3-二醇
  参考文献：
  名称：

  一种马沙骨化醇的制备方法

  摘要：

  本发明涉及一种药物的合成方法，特别涉及一种马沙骨化醇的制备方法。以脱氢表雄酮为起始原料，经酰化、格氏反应、氧化、皂化、羟基保护、环氧化、还原、消除、NBS溴代/脱溴化氢、脱保护基、光照开环制备得到马沙骨化醇，操作简单、收率高，适合大规模工业化生产。

  公开号：

  CN114656385A

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。
• Ultraviolet irradiation apparatus for photochemical reaction and preparation process of vitamin D derivative making use of the same
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20040108198A1

  公开（公告）日：2004-06-10

  Disclosed herein are an ultraviolet irradiation apparatus for photochemical reactions which can irradiate the photo-reactive solution with ultraviolet rays having a specific wavelength suitable for the intended photochemical reaction at a high efficiency, and a process by which a provitamin D derivative can be converted into a provitamin D derivative at a high efficiency by means of a photochemical reaction by one-step process of light irradiation, thereby preparing a vitamin D derivative at a high efficiency. The ultraviolet irradiation apparatus irradiates the photo-reactive solution with the ultraviolet rays having the specific wavelength through a quartz rod. Specifically, the apparatus is constructed by an electric discharge lamp, a condensing and reflecting mirror and a plane mirror both having wavelength selective property, an optical filter which transmits the ultraviolet rays having the specific wavelength, and a quartz rod on which the ultraviolet rays having the specific wavelength are struck. The photo-reactive solution is irradiated with the ultraviolet rays from the quartz rod. The quartz rod is immersed in the photo-reactive solution, or a reaction vessel is irradiated with the ultraviolet rays from the quartz rod. In the preparation process of the vitamin D derivative, an ultraviolet irradiation apparatus for photochemical reactions having an ultraviolet radiation-emitting lamp, an optical system having wavelength selective property and a quartz rod on which the ultraviolet rays having the specific wavelength from the optical system are struck is used, and a solution of a provitamin D derivative is irradiated with the ultraviolet rays having the specific wavelength emitted from the quartz rod to cause a photochemical reaction of the provitamin D derivative solution, thereby forming a previtamin D derivative. The previtamin D derivative is further subjected to a thermal isomerization reaction to prepare the vitamin D derivative.

  本文披露了一种用于光化学反应的紫外辐射装置，该装置可以以高效率照射具有特定波长的紫外线的光敏反应溶液，适用于预期的光化学反应，并通过光照的一步法将一种类维生素D衍生物转化为高效率的类维生素D衍生物的过程，从而高效率地制备维生素D衍生物。紫外辐射装置通过石英棒以特定波长的紫外线照射光敏反应溶液。具体而言，该装置由电放电灯、具有波长选择性的聚焦和反射镜和平面镜、透射具有特定波长的紫外线的光学滤波器以及被特定波长的紫外线击中的石英棒构成。光敏反应溶液从石英棒处照射出紫外线。石英棒浸泡在光敏反应溶液中，或者光敏反应溶液从石英棒处照射到反应容器中。在维生素D衍生物的制备过程中，使用一种用于光化学反应的紫外辐射装置，该装置具有紫外辐射发射灯、具有波长选择性的光学系统和石英棒，光学系统发出具有特定波长的紫外线，用于照射类维生素D衍生物溶液，从而引发类维生素D衍生物溶液的光化学反应，形成前维生素D衍生物。进一步对前维生素D衍生物进行热异构化反应，制备维生素D衍生物。
• 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。
• Synthetic Studies of Vitamin D Analogues. XI. Synthesis and Differentiation-Inducing Activity of 1.ALPHA.,25-Dihydroxy-22-oxavitamin D3 Analogues.
  作者：Noboru KUBODERA、Hiroyoshi WATANABE、Takehiko KAWANISHI、Masahiko MATSUMOTO

  DOI：10.1248/cpb.40.1494

  日期：——

  Six analogues of 1α, 25-dihydroxy-22-oxavitamin D3 (OCT) (2), 26, 27-dimethyl OCT (5), 26, 27-diethyl OCT (6), 24-norOCT (7), 24-homoOCT (8), 24-dihomoOCT (9), and 24-trihomoOCT (10) were synthesized from the 20(S)-alcohol (11) as the common starting material. In the activity inducing differentiation of human myeloid leukemia cells (HL-60) into macrophages, 26, 27-dimethyl OCT (5) and 24-homoOCT (8) showed the highest activities. The binding properties of these analogues to the chick embryonic intestinal 1α, 25-dihydroxyvitamin D3 (1) receptor are also described.

  1α, 25-二羟基-22-奥沙维他命 D3 (OCT) (2)、26, 27-二甲基 OCT (5)、26, 27-二乙基 OCT (6)、24-norOCT (7)、24-homoOCT 的六种类似物(8)、24-dihomoOCT (9) 和 24-trihomoOCT (10) 由 20(S)-醇 (11) 作为共同起始原料合成。在诱导人骨髓性白血病细胞（HL-60）向巨噬细胞分化的活性中，26, 27-二甲基OCT（5）和24-homoOCT（8）表现出最高活性。还描述了这些类似物与鸡胚肠道 1α, 25-二羟基维生素 D3 (1) 受体的结合特性。
• Novel procedure for the preparation of 1α,3β-dihydroxy-2β-tritiated steroidal compounds
  作者：Hiroyoshi Watanabe、Takehiko Kawanishi、Katsuhito Miyamoto、Noboru Kubodera、Kazuo Sasahara、Kiyoshige Ochi

  DOI：10.1016/0039-128x(92)90098-t

  日期：1992.9

  Abstract A novel procedure for the preparation of 1α,3β-dihydroxy-2β-tritiated steroidal compounds by the reduction of the α-epoxide with sodium horotritiide in diglyme at 80 C is described.

  摘要描述了一种通过在 80°C 下在二甘醇二甲醚中用 horotritiide 钠还原 α-环氧化物来制备 1α,3β-二羟基-2β-氚化甾族化合物的新方法。