(4S,5R,6R,8R)-6-diphenylphosphoryl-8-phenylmethoxydodecane-1,4,5-triol | 204506-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5R,6R,8R)-6-diphenylphosphoryl-8-phenylmethoxydodecane-1,4,5-triol
• CAS: 204506-10-5
• 化学式: C₃₁H₄₁O₅P
• 分子量: 524.637
• InChiKey: APEHVYCDEJHYBT-HMAILUFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R,8R)-6-diphenylphosphoryl-8-phenylmethoxydodecane-1,4,5-triol 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以27%的产率得到(4S,5E,8R)-8-Benzyloxydodec-5-ene-1,4-diol
  参考文献：
  名称：

  Alkenyl diols by E-selective Horner-Wittig elimination: Formal synthesis of any isomer (RR, RS, SR or SS) bearing 1,5-related stereogenic centres across an E double bond

  摘要：

  Oxidation of diastereomerically pure diphenylphosphinoyl furans [e.g. 4-benzyloxy-2-diphenylphosphinoyl 1-(2'-furyl) octan-1-ol] with m-CPBA, followed by reduction with sodium borohydride, gives triols with four stereochemically controlled stereogenic centres. (E)-Selective Horner-Wittig elimination removes the middle two stereogenic centres to yield diols with 1,5-related stereogenic centres across a trans double bond. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10859-0
• 作为产物：
  描述：

  2-呋喃甲基乙酯 在 sodium tetrahydroborate 、 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (4S,5R,6R,8R)-6-diphenylphosphoryl-8-phenylmethoxydodecane-1,4,5-triol
  参考文献：
  名称：

  Alkenyl diols by E-selective Horner-Wittig elimination: Formal synthesis of any isomer (RR, RS, SR or SS) bearing 1,5-related stereogenic centres across an E double bond

  摘要：

  Oxidation of diastereomerically pure diphenylphosphinoyl furans [e.g. 4-benzyloxy-2-diphenylphosphinoyl 1-(2'-furyl) octan-1-ol] with m-CPBA, followed by reduction with sodium borohydride, gives triols with four stereochemically controlled stereogenic centres. (E)-Selective Horner-Wittig elimination removes the middle two stereogenic centres to yield diols with 1,5-related stereogenic centres across a trans double bond. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10859-0

文献信息

• Alkenyl diols by E-selective Horner-Wittig elimination: Formal synthesis of any isomer (RR, RS, SR or SS) bearing 1,5-related stereogenic centres across an E double bond
  作者：Adam Nelson、Stuart Warren

  DOI：10.1016/s0040-4039(97)10859-0

  日期：1998.3

  Oxidation of diastereomerically pure diphenylphosphinoyl furans [e.g. 4-benzyloxy-2-diphenylphosphinoyl 1-(2'-furyl) octan-1-ol] with m-CPBA, followed by reduction with sodium borohydride, gives triols with four stereochemically controlled stereogenic centres. (E)-Selective Horner-Wittig elimination removes the middle two stereogenic centres to yield diols with 1,5-related stereogenic centres across a trans double bond. (C) 1998 Elsevier Science Ltd. All rights reserved.