1,4:3,6-dianhydro-2-O-benzyl-5-O-(2-diethylphosphono-2-fluoro)acetyl-D-mannitol | 569686-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1,4:3,6-dianhydro-2-O-benzyl-5-O-(2-diethylphosphono-2-fluoro)acetyl-D-mannitol
• 英文别名: [(3R,3aR,6R,6aR)-3-phenylmethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] 2-diethoxyphosphoryl-2-fluoroacetate
• CAS: 569686-38-0
• 化学式: C₁₉H₂₆FO₈P
• 分子量: 432.383
• InChiKey: DBDDRXCENAXKRO-XNIMBYMISA-N

物化性质

• 沸点：
  531.7±50.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-叔丁基环己酮 、 1,4:3,6-dianhydro-2-O-benzyl-5-O-(2-diethylphosphono-2-fluoro)acetyl-D-mannitol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.0h， 生成 (aR)-1,4:3,6-dianhydro-2-O-benzyl-5-O-[2-(4-tert-butylcyclohexylidene)-2-fluoroacetyl]-D-mannitol 、 (aS)-1,4:3,6-dianhydro-2-O-benzyl-5-O-[2-(4-tert-butylcyclohexylidene)-2-fluoroacetyl]-D-mannitol
  参考文献：
  名称：

  Asymmetric Horner-Wadsworth-Emmons Reaction Utilizing Isomannide and Iso- sorbide Derivatives as Chiral Auxiliaries

  摘要：

  The diastereoselective Horner-Wadsworth-Emmons reaction of chiral phosphonates with sigma-symmetric 4-tert-butylcyclohexanone and 4phenylcyclohexanone was investigated by employing isomannide and isosorbide derivatives as chiral auxiliaries. alpha-Fluoro-alpha,beta-unsaturated esters with an axis of chirality were obtained in diastereomer ratio up to 14 : 86 (aR : aS).

  DOI：

  10.3987/com-02-s82
• 作为产物：
  描述：

  1,4:3,6-dianhydro-D-mannitol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 1,4:3,6-dianhydro-2-O-benzyl-5-O-(2-diethylphosphono-2-fluoro)acetyl-D-mannitol
  参考文献：
  名称：

  Asymmetric Horner-Wadsworth-Emmons Reaction Utilizing Isomannide and Iso- sorbide Derivatives as Chiral Auxiliaries

  摘要：

  The diastereoselective Horner-Wadsworth-Emmons reaction of chiral phosphonates with sigma-symmetric 4-tert-butylcyclohexanone and 4phenylcyclohexanone was investigated by employing isomannide and isosorbide derivatives as chiral auxiliaries. alpha-Fluoro-alpha,beta-unsaturated esters with an axis of chirality were obtained in diastereomer ratio up to 14 : 86 (aR : aS).

  DOI：

  10.3987/com-02-s82

文献信息

• Asymmetric Horner-Wadsworth-Emmons Reaction Utilizing Isomannide and Iso- sorbide Derivatives as Chiral Auxiliaries
  作者：Shigeki Sano、Rie Teranishi、Fumihito Nakano、Kyougetu In、Hiroe Takeshige、Takahiro Ishii、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.3987/com-02-s82

  日期：——

  The diastereoselective Horner-Wadsworth-Emmons reaction of chiral phosphonates with sigma-symmetric 4-tert-butylcyclohexanone and 4phenylcyclohexanone was investigated by employing isomannide and isosorbide derivatives as chiral auxiliaries. alpha-Fluoro-alpha,beta-unsaturated esters with an axis of chirality were obtained in diastereomer ratio up to 14 : 86 (aR : aS).