methyl 3β-diphenylphosphorylchol-5-enoate | 1579253-65-8

• 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: methyl 3β-diphenylphosphorylchol-5-enoate
• 英文别名: methyl (4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-[oxido(diphenoxy)phosphaniumyl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1579253-65-8
• 化学式: C₃₇H₄₉O₆P
• 分子量: 620.766
• InChiKey: MWRIQAYTJOVUCW-RMCWQMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3β-diphenylphosphorylchol-5-enoate 、 双丙酮半乳糖 在 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 以37%的产率得到methyl 3β-O-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)chol-5-enoate
  参考文献：
  名称：

  Electrochemical synthesis of glycoconjugates from activated sterol derivatives

  摘要：

  Several derivatives of cholesterol and other 3 beta-hydroxy-Delta(5)-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.007
• 作为产物：
  描述：

  (3b)-3-羟基-胆-5-烯-24-酸甲酯 、 氯磷酸二苯酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以87%的产率得到methyl 3β-diphenylphosphorylchol-5-enoate
  参考文献：
  名称：

  Electrochemical synthesis of glycoconjugates from activated sterol derivatives

  摘要：

  Several derivatives of cholesterol and other 3 beta-hydroxy-Delta(5)-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.007

文献信息

• Electrochemical synthesis of glycoconjugates from activated sterol derivatives
  作者：Aneta M. Tomkiel、Jan Kowalski、Jolanta Płoszyńska、Leszek Siergiejczyk、Zenon Łotowski、Andrzej Sobkowiak、Jacek W. Morzycki

  DOI：10.1016/j.steroids.2014.01.007

  日期：2014.4

  Several derivatives of cholesterol and other 3 beta-hydroxy-Delta(5)-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors. (C) 2014 Elsevier Inc. All rights reserved.