(4S,5R)-(2,2-dimethoxyethyl)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-ylmethyl)carbamic acid methylester | 1155303-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-(2,2-dimethoxyethyl)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-ylmethyl)carbamic acid methylester
• 英文别名: methyl N-(2,2-dimethoxyethyl)-N-[[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]carbamate
• CAS: 1155303-24-4
• 化学式: C₁₃H₂₅NO₇
• 分子量: 307.344
• InChiKey: UTEAFVPHVVZHPW-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R)-(2,2-dimethoxyethyl)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-ylmethyl)carbamic acid methylester 、 溴甲苯 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以67%的产率得到(4S,5R)-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-(2,2-dimethoxyethyl)carbamic acid methyl ester
  参考文献：
  名称：

  N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-amino alcohols

  摘要：

  Chiral enantiopure bicyclic 1,4-aminoalcohols were synthesised by a new methodology that provided a common precursor, which was easily N-functionalised with a wide variety of substituents. The final compounds were used as chiral ligands in a model study of the enantioselective addition of diethyl zinc to benzaldehyde, aimed at understanding the influence of the N-substituent on both the rate and stereoselectivity of the reaction. This set of experiments also provided interesting insight into the non-catalysed addition that Occurred by employing commercially available Et(2)Zn solutions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.021
• 作为产物：
  描述：

  (4S,5R)-{5-[(2,2-dimethoxyethylamino)methyl]-2,2-dimethyl[1,3]dioxolan-4-yl}methanol 、 氯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以86%的产率得到(4S,5R)-(2,2-dimethoxyethyl)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-ylmethyl)carbamic acid methylester
  参考文献：
  名称：

  N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-amino alcohols

  摘要：

  Chiral enantiopure bicyclic 1,4-aminoalcohols were synthesised by a new methodology that provided a common precursor, which was easily N-functionalised with a wide variety of substituents. The final compounds were used as chiral ligands in a model study of the enantioselective addition of diethyl zinc to benzaldehyde, aimed at understanding the influence of the N-substituent on both the rate and stereoselectivity of the reaction. This set of experiments also provided interesting insight into the non-catalysed addition that Occurred by employing commercially available Et(2)Zn solutions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.021

文献信息

• N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-amino alcohols
  作者：Dina Scarpi、Ernesto G. Occhiato、Antonio Guarna

  DOI：10.1016/j.tetasy.2009.01.021

  日期：2009.2

  Chiral enantiopure bicyclic 1,4-aminoalcohols were synthesised by a new methodology that provided a common precursor, which was easily N-functionalised with a wide variety of substituents. The final compounds were used as chiral ligands in a model study of the enantioselective addition of diethyl zinc to benzaldehyde, aimed at understanding the influence of the N-substituent on both the rate and stereoselectivity of the reaction. This set of experiments also provided interesting insight into the non-catalysed addition that Occurred by employing commercially available Et(2)Zn solutions. (C) 2009 Elsevier Ltd. All rights reserved.