N-(3-deoxy-1,2-O-isopropylidene-1.4-D-xylo-furanylidene)benzylamine | 131196-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3-deoxy-1,2-O-isopropylidene-1.4-D-xylo-furanylidene)benzylamine
• CAS: 131196-34-4
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: PKKLFSHEZYTLAF-QLDGQODYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethylene glycol trans-1-(trimethylsilyl)-1-propane-3-boronate 、 N-(3-deoxy-1,2-O-isopropylidene-1.4-D-xylo-furanylidene)benzylamine 以 四氯化碳 为溶剂， 以85%的产率得到N-benzyl-1-(3-deoxy-1,2-O-isopropylidene-1,4-furanosyl-α-D-xylo-pentyl)-2-(trimethylsilyl)-3-butenylamine
  参考文献：
  名称：

  The addition of .gamma.-(trimethylsilyl)allylboronates to imines

  摘要：

  The addition of gamma-(trimethylsilyl)allylboronates to imines is described and compared with the addition of simple allylboronates to imines. The addition of gamma-(trimethylsilyl)allylboronates to imines is found to be more efficient than the addition of simple allylboronates to imines. The stereoselectivity is dependant upon the nature of the imine; imines derived from aromatic aldehydes give anti products and imines derived from aliphatic aldehydes give syn products. Proof of stereochemistry was established by conversion of the anti and syn derivatives to their respective Z- and E-dienes by a methylation/E-2 elimination process. With alpha-alkoxy aldehydes the reaction proceeds with excellent selectivity giving the product of Felkin-Ahn addition.

  DOI：

  10.1021/jo00001a067
• 作为产物：
  描述：

  O¹,O²-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose 、 苄胺 反应 1.0h， 以76%的产率得到N-(3-deoxy-1,2-O-isopropylidene-1.4-D-xylo-furanylidene)benzylamine
  参考文献：
  名称：

  The addition of .gamma.-(trimethylsilyl)allylboronates to imines

  摘要：

  The addition of gamma-(trimethylsilyl)allylboronates to imines is described and compared with the addition of simple allylboronates to imines. The addition of gamma-(trimethylsilyl)allylboronates to imines is found to be more efficient than the addition of simple allylboronates to imines. The stereoselectivity is dependant upon the nature of the imine; imines derived from aromatic aldehydes give anti products and imines derived from aliphatic aldehydes give syn products. Proof of stereochemistry was established by conversion of the anti and syn derivatives to their respective Z- and E-dienes by a methylation/E-2 elimination process. With alpha-alkoxy aldehydes the reaction proceeds with excellent selectivity giving the product of Felkin-Ahn addition.

  DOI：

  10.1021/jo00001a067