tert-butyl [(4R,6S)-6-(1-hydroxy-2-nitroethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate | 619261-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl [(4R,6S)-6-(1-hydroxy-2-nitroethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate
• 英文别名: tert-butyl 2-[(4R,6S)-6-[(1R)-1-hydroxy-2-nitroethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate
• CAS: 619261-19-7
• 化学式: C₁₄H₂₅NO₇
• 分子量: 319.355
• InChiKey: JAKJLSVXXZUPEI-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl [(4R,6S)-6-(1-hydroxy-2-nitroethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 4.0h， 生成 6-氨乙基-2,2-二甲基-1,3-二氧六环-4-乙酸叔丁酯
  参考文献：
  名称：

  A New Way totert-Butyl [(4R,6R)-6-Aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a Key Intermediate of Atorvastatin Synthesis

  摘要：

  A new synthesis of tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a key intermediate of the synthesis of an effective HMG-CoA reductase inhibitor atorvastatin, is described. The synthesis is based on the Henry reaction of nitromethane and tert-butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl] acetate. The formed nitroaldol was then O-acetylated and the sodium borohydride reduction of the intermediate provided tert-butyl [(4R,6R)-2,2-dimethyl-6-nitroethyl-1,3-dioxan-4-yl] acetate. Catalytic hydrogenation of the nitro group led to the title compound.

  DOI：

  10.1081/scc-120021507
• 作为产物：
  描述：

  (4R-Cis)-6-羟甲基-2,2-二甲基-1,3-二氧六环-4-乙酸叔丁酯 在 potassium fluoride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 5.0h， 生成 tert-butyl [(4R,6S)-6-(1-hydroxy-2-nitroethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate
  参考文献：
  名称：

  A New Way totert-Butyl [(4R,6R)-6-Aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a Key Intermediate of Atorvastatin Synthesis

  摘要：

  A new synthesis of tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a key intermediate of the synthesis of an effective HMG-CoA reductase inhibitor atorvastatin, is described. The synthesis is based on the Henry reaction of nitromethane and tert-butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl] acetate. The formed nitroaldol was then O-acetylated and the sodium borohydride reduction of the intermediate provided tert-butyl [(4R,6R)-2,2-dimethyl-6-nitroethyl-1,3-dioxan-4-yl] acetate. Catalytic hydrogenation of the nitro group led to the title compound.

  DOI：

  10.1081/scc-120021507

文献信息

• A New Way to<i>tert</i>-Butyl [(4<i>R</i>,6<i>R</i>)-6-Aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a Key Intermediate of Atorvastatin Synthesis
  作者：Stanislav Rádl

  DOI：10.1081/scc-120021507

  日期：2003.1.7

  A new synthesis of tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a key intermediate of the synthesis of an effective HMG-CoA reductase inhibitor atorvastatin, is described. The synthesis is based on the Henry reaction of nitromethane and tert-butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl] acetate. The formed nitroaldol was then O-acetylated and the sodium borohydride reduction of the intermediate provided tert-butyl [(4R,6R)-2,2-dimethyl-6-nitroethyl-1,3-dioxan-4-yl] acetate. Catalytic hydrogenation of the nitro group led to the title compound.