(7E)-(3S,6S)-6,19-epithio-9,10-seco-5(10),7,22-ergostatrien-3-ol S,S-dioxide

• 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: (7E)-(3S,6S)-6,19-epithio-9,10-seco-5(10),7,22-ergostatrien-3-ol S,S-dioxide
• 英文别名: (3S,5S)-3-[(E)-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]methyl]-2,2-dioxo-1,3,4,5,6,7-hexahydro-2-benzothiophen-5-ol
• 化学式: C₂₈H₄₄O₃S
• 分子量: 460.722
• InChiKey: LYTLCKCMCADGOA-SFMWDCSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (7E)-(3S,6S)-6,19-epithio-9,10-seco-5(10),7,22-ergostatrien-3-ol S,S-dioxide 在 咪唑 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.08h， 生成 (叔丁基)[(3beta,5E,7E,22E)-9,10-开环麦角甾-5,7,10(19),22-四烯-3-基氧基]二甲基硅烷
  参考文献：
  名称：

  Development of an Improved Process for Doxercalciferol via a Continuous Photochemical Reaction

  摘要：

  Doxercalciferol (1 alpha-hydroxyvitamin D2) is a commercially approved vitamin D derivative used to treat chronic kidney disease (CKD) patients whose kidneys cannot metabolically introduce a hydroxyl group at C1. A new process for the production of doxercalciferol from ergocalciferol was developed using a continuous photoisomerization of a known vitamin D intermediate as the key step, thus circumventing the limitations of batch photoisomerization processes. Doxercalciferol is produced in an overall yield of about 10% from ergocalciferol.

  DOI：

  10.1021/op200346g
• 作为产物：
  描述：

  维生素D2 在 二氧化硫 、 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 0.38h， 生成 (7E)-(3S,6S)-6,19-epithio-9,10-seco-5(10),7,22-ergostatrien-3-ol S,S-dioxide
  参考文献：
  名称：

  Development of an Improved Process for Doxercalciferol via a Continuous Photochemical Reaction

  摘要：

  Doxercalciferol (1 alpha-hydroxyvitamin D2) is a commercially approved vitamin D derivative used to treat chronic kidney disease (CKD) patients whose kidneys cannot metabolically introduce a hydroxyl group at C1. A new process for the production of doxercalciferol from ergocalciferol was developed using a continuous photoisomerization of a known vitamin D intermediate as the key step, thus circumventing the limitations of batch photoisomerization processes. Doxercalciferol is produced in an overall yield of about 10% from ergocalciferol.

  DOI：

  10.1021/op200346g

文献信息

• Synthesis of 24(28)-Methylene-1α-Hydroxyvitamin D₃, a Novel Vitamin D₃ Analogue
  作者：Wei Guo、Zhijie Fang、Hongliang Li、Yanan Liu

  DOI：10.3184/174751914x13941144023496

  日期：2014.4

  24(28)-Methylene-1α-hydroxyvitamin D3 was synthesised in 13 steps from vitamin D2. The key step of the synthesis involved the Wittig–Horner olefination of a nor-vitamin D2 aldehyde with diethylphosphono-3-methyl-2-butanone. The resulting enone was followed by reduced methylenation, photoisomerisation and deprotection then gave the target compound.

  24(28)-亚甲基-1α-羟基维生素 D3 由维生素 D2 分 13 步合成。合成的关键步骤涉及去甲维生素 D2 醛与二乙基膦酰基-3-甲基-2-丁酮的 Wittig-Horner 烯化。所得烯酮随后进行还原亚甲基化、光异构化和脱保护，然后得到目标化合物。
• Development of an Improved Process for Doxercalciferol via a Continuous Photochemical Reaction
  作者：Bruce G. Anderson、William E. Bauta、William R. Cantrell

  DOI：10.1021/op200346g

  日期：2012.5.18

  Doxercalciferol (1 alpha-hydroxyvitamin D2) is a commercially approved vitamin D derivative used to treat chronic kidney disease (CKD) patients whose kidneys cannot metabolically introduce a hydroxyl group at C1. A new process for the production of doxercalciferol from ergocalciferol was developed using a continuous photoisomerization of a known vitamin D intermediate as the key step, thus circumventing the limitations of batch photoisomerization processes. Doxercalciferol is produced in an overall yield of about 10% from ergocalciferol.