(4R,5R,3'S,4'R)-5-(2'-aza-2',3'-dimethyl-4'-hydroxy-4'-phenyl-butyl)-2,2-dimethyl-4-phenyl-1,3-dioxane | 223394-33-0

• 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: (4R,5R,3'S,4'R)-5-(2'-aza-2',3'-dimethyl-4'-hydroxy-4'-phenyl-butyl)-2,2-dimethyl-4-phenyl-1,3-dioxane
• 英文别名: (1R,2S)-2-[[(4R,5R)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]methyl-methylamino]-1-phenylpropan-1-ol
• CAS: 223394-33-0
• 化学式: C₂₃H₃₁NO₃
• 分子量: 369.504
• InChiKey: CRZMVJVLPPASMS-XGARDCMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R,3'S,4'R)-5-(2'-aza-2',3'-dimethyl-4'-hydroxy-4'-phenyl-butyl)-2,2-dimethyl-4-phenyl-1,3-dioxane 、 碘甲烷 反应 48.0h， 生成 ((4R,5R)-2,2-Dimethyl-4-phenyl-[1,3]dioxan-5-ylmethyl)-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-dimethyl-ammonium; iodide
  参考文献：
  名称：

  Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate

  摘要：

  Deprotonation of chiral masked synthetic equivalents of ethyl glyoxalate, derived from norephedrine, with a novel base formed by addition of tert-BuLi to tert-butyl formate. and subsequent reaction with aromatic aldehydes yields P-hydroxy esters in good yield and moderate to excellent diastereomeric excesses. Reductive transformation of the condensation products, and elimination of the chiral appendage leads to enantiomerically pure 2-aminomethyl-1,3-propanediol derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00046-0
• 作为产物：
  描述：

  (1'R,2'R,2S,4S,5R)-N-ethoxycarbonyl-2-(1'-ethoxycarbonyl-2'-phenyl-1-hydroxyethyl)-4-methyl-5-phenyl-1,3-oxazolidine 在 lithium aluminium tetrahydride 、 三氯化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 12.25h， 生成 (4R,5R,3'S,4'R)-5-(2'-aza-2',3'-dimethyl-4'-hydroxy-4'-phenyl-butyl)-2,2-dimethyl-4-phenyl-1,3-dioxane
  参考文献：
  名称：

  Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate

  摘要：

  Deprotonation of chiral masked synthetic equivalents of ethyl glyoxalate, derived from norephedrine, with a novel base formed by addition of tert-BuLi to tert-butyl formate. and subsequent reaction with aromatic aldehydes yields P-hydroxy esters in good yield and moderate to excellent diastereomeric excesses. Reductive transformation of the condensation products, and elimination of the chiral appendage leads to enantiomerically pure 2-aminomethyl-1,3-propanediol derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00046-0

文献信息

• Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate
  作者：María García-Valverde、Javier Nieto、Rafael Pedrosa、Martina Vicente

  DOI：10.1016/s0040-4020(99)00046-0

  日期：1999.2

  Deprotonation of chiral masked synthetic equivalents of ethyl glyoxalate, derived from norephedrine, with a novel base formed by addition of tert-BuLi to tert-butyl formate. and subsequent reaction with aromatic aldehydes yields P-hydroxy esters in good yield and moderate to excellent diastereomeric excesses. Reductive transformation of the condensation products, and elimination of the chiral appendage leads to enantiomerically pure 2-aminomethyl-1,3-propanediol derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.