(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate | 1564245-55-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS: 1564245-55-1
• 化学式: C₂₁H₃₂BNO₆
• 分子量: 405.299
• InChiKey: UEODCOFIOXFVSS-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate 在 盐酸 、 sodium perborate tetrahydrate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 7.0h， 生成 H-Phe(β-OH)-OMe*HCl
  参考文献：
  名称：

  Copper-Catalyzed Asymmetric Hydroboration of α-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β-Hydroxy-α-amino Acids

  摘要：

  The Cu-catalyzed asymmetric conjugate hydroboration reaction of beta-substituted alpha-dehydroamino acid derivatives has been established, affording enantioenriched syn- and anti-beta-boronate-alpha-amino acid derivatives with excellent combined yields (83-99%, dr approximate to 1:1) and excellent enantioselectivities (92-98% ee). The hydroboration products were expediently converted into valuable beta-hydroxy-alpha-amino acid derivatives, which were widely used in the preparation of chiral drugs and bioactive molecules.

  DOI：

  10.1021/ol500219e
• 作为产物：
  描述：

  苯甲醛 在 (R,R)-QuinoxP 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.5h， 生成 (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate 、 (2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
  参考文献：
  名称：

  Copper-Catalyzed Asymmetric Hydroboration of α-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β-Hydroxy-α-amino Acids

  摘要：

  The Cu-catalyzed asymmetric conjugate hydroboration reaction of beta-substituted alpha-dehydroamino acid derivatives has been established, affording enantioenriched syn- and anti-beta-boronate-alpha-amino acid derivatives with excellent combined yields (83-99%, dr approximate to 1:1) and excellent enantioselectivities (92-98% ee). The hydroboration products were expediently converted into valuable beta-hydroxy-alpha-amino acid derivatives, which were widely used in the preparation of chiral drugs and bioactive molecules.

  DOI：

  10.1021/ol500219e