tert-butyl 5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2,4-dideoxy-2-methyl-D-erythropentonate | 1448551-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl 5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2,4-dideoxy-2-methyl-D-erythropentonate
• 英文别名: tert-butyl (2R,3R)-5-[bis(4-methoxyphenyl)-phenylmethoxy]-3-hydroxy-2-methylpentanoate
• CAS: 1448551-47-0
• 化学式: C₃₁H₃₈O₆
• 分子量: 506.639
• InChiKey: TZKVVEDYZQPCPI-SKCUWOTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙烯酸叔丁酯 以 乙醚 为溶剂， 反应 20.0h， 生成 tert-butyl 5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2,4-dideoxy-2-methyl-D-erythropentonate 、 tert-butyl 5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2,4-dideoxy-2-methylpentonate
  参考文献：
  名称：

  (Diisopinocampheyl)borane-Mediated Reductive Aldol Reactions of Acrylate Esters: Enantioselective Synthesis of Anti-Aldols

  摘要：

  The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-alpha-methyl-beta-hydroxy esters 9 or 10 with excellent diastereo- (up to >= 20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.

  DOI：

  10.1021/ol401679g