(1R,2S,5R,6R)-3-aza-1-phenyl-6-furyl-5-hydroxymethyl-2,3-dimethyl-1,6-hexanediol | 223394-32-9

• 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: (1R,2S,5R,6R)-3-aza-1-phenyl-6-furyl-5-hydroxymethyl-2,3-dimethyl-1,6-hexanediol
• CAS: 223394-32-9
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: LFVFVRRIWKULQM-UNQWWWNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77.07
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (1R,2S,5R,6R)-3-aza-1-phenyl-6-furyl-5-hydroxymethyl-2,3-dimethyl-1,6-hexanediol 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 (4R,5R,3'S,4'R)-5-(2'-aza-2',3'-dimethyl-4'-hydroxy-4'-phenyl-butyl)-2,2-dimethyl-4-furyl-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
• 作为产物：
  描述：

  (1'R,2'R,2S,4S,5R)-N-ethoxycarbonyl-2-(1'-ethoxycarbonyl-2'-furyl-2'-hydroxyethyl)-4-methyl-5-phenyl-1,3-oxazolidine 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以80%的产率得到(1R,2S,5R,6R)-3-aza-1-phenyl-6-furyl-5-hydroxymethyl-2,3-dimethyl-1,6-hexanediol
  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