tert-butyl (2S,3R,4S)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate | 1029289-50-6

• 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: tert-butyl (2S,3R,4S)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S,3R,4S)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-yl]carbamate
• CAS: 1029289-50-6
• 化学式: C₁₈H₂₈N₂O₇
• 分子量: 384.43
• InChiKey: IWDKJPJKRDGJNF-SOUVJXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R,4S)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Stereodivergent Catalytic Doubly Diastereoselective Nitroaldol Reactions Using Heterobimetallic Complexes

  摘要：

  Stereodivergent construction of three contiguous stereocenters in catalytic doubly diastereoselective nitroaldol reactions of a-chiral aldehydes with nitroacetaldehyde dimethyl acetal using two types of heterobimetallic catalysts is described. A La-Li-BINOL (LLB) catalyst afforded anti,syn-nitroaldol products in >20:1-14:1 selectivity, and a Pd/La/Schiff base catalyst afforded complimentary syn,syn-nitroaldol products in 10:1-5:1 selectivity.

  DOI：

  10.1021/ol800653d
• 作为产物：
  描述：

  硝基乙醛缩二甲醇 、 N-Boc-L-苯丙氨醛 在 C₂₆H₂₂BrLaN₂O₅Pd 作用下， 以 四氢呋喃 、 xylenes 为溶剂， 反应 73.0h， 以87%的产率得到tert-butyl (2S,3R,4S)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate
  参考文献：
  名称：

  Stereodivergent Catalytic Doubly Diastereoselective Nitroaldol Reactions Using Heterobimetallic Complexes

  摘要：

  Stereodivergent construction of three contiguous stereocenters in catalytic doubly diastereoselective nitroaldol reactions of a-chiral aldehydes with nitroacetaldehyde dimethyl acetal using two types of heterobimetallic catalysts is described. A La-Li-BINOL (LLB) catalyst afforded anti,syn-nitroaldol products in >20:1-14:1 selectivity, and a Pd/La/Schiff base catalyst afforded complimentary syn,syn-nitroaldol products in 10:1-5:1 selectivity.

  DOI：

  10.1021/ol800653d

文献信息

• Stereodivergent Catalytic Doubly Diastereoselective Nitroaldol Reactions Using Heterobimetallic Complexes
  作者：Yoshihiro Sohtome、Yuko Kato、Shinya Handa、Naohiro Aoyama、Keita Nagawa、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ol800653d

  日期：2008.6.5

  Stereodivergent construction of three contiguous stereocenters in catalytic doubly diastereoselective nitroaldol reactions of a-chiral aldehydes with nitroacetaldehyde dimethyl acetal using two types of heterobimetallic catalysts is described. A La-Li-BINOL (LLB) catalyst afforded anti,syn-nitroaldol products in >20:1-14:1 selectivity, and a Pd/La/Schiff base catalyst afforded complimentary syn,syn-nitroaldol products in 10:1-5:1 selectivity.