(2S,4R)-1-benzyloxycarbonyl-4-<(tert-butyldimethylsilyl)oxy>-2-<(diisopropylphosphono)methyl>-pyrrolidine | 172511-98-7

• 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: (2S,4R)-1-benzyloxycarbonyl-4-<(tert-butyldimethylsilyl)oxy>-2-<(diisopropylphosphono)methyl>-pyrrolidine
• 英文别名: benzyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[di(propan-2-yloxy)phosphorylmethyl]pyrrolidine-1-carboxylate
• CAS: 172511-98-7
• 化学式: C₂₅H₄₄NO₆PSi
• 分子量: 513.687
• InChiKey: DCIISAALBJFYLH-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-benzyloxycarbonyl-4-<(tert-butyldimethylsilyl)oxy>-2-<(diisopropylphosphono)methyl>-pyrrolidine 在 palladium on activated charcoal 草酰氯 、 氢气 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 39.5h， 生成 (2S,4S)-1-benzyl-2-<(diisopropylphosphonyl)methyl>pyrrolidine-4-spiro-5'-hydantoin
  参考文献：
  名称：

  Synthesis of homochiral 4-amino-4-carboxy-2-phosphonomethylpyrrolidines via a diastereoselective bucherer-bergs reaction of 4-oxopyrrolidine derivative: Novel conformationally restricted AP 5 analogues

  摘要：

  Asymmetric synthesis of 4-amino-4-carboxy-2-phosphonomethylpyrrolidines 1 and 2, which can be viewed as novel conformationally restricted analogues of 2-amino-5-phosphonopentanoic acid (AP 5) incorporated into the pyrrolidine ring, was achieved from trans-4-hydroxy-L-proline as a homochiral starting material using the diastereoselective Bucherer-Bergs reaction of(2S)-1-benzyl-2-[(diisopropylphosphonyl)methyl]-4-oxopyrrolidine 12.

  DOI：

  10.1016/0957-4166(95)00302-6
• 作为产物：
  描述：

  (2S,4R)-1-benzyloxycarbonyl-4-<(tert-butyldimethylsilyl)oxy>-2-(hydroxymethyl)pyrrolidine 在 咪唑 、 碘 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 25.0h， 生成 (2S,4R)-1-benzyloxycarbonyl-4-<(tert-butyldimethylsilyl)oxy>-2-<(diisopropylphosphono)methyl>-pyrrolidine
  参考文献：
  名称：

  Synthesis of homochiral 4-amino-4-carboxy-2-phosphonomethylpyrrolidines via a diastereoselective bucherer-bergs reaction of 4-oxopyrrolidine derivative: Novel conformationally restricted AP 5 analogues

  摘要：

  Asymmetric synthesis of 4-amino-4-carboxy-2-phosphonomethylpyrrolidines 1 and 2, which can be viewed as novel conformationally restricted analogues of 2-amino-5-phosphonopentanoic acid (AP 5) incorporated into the pyrrolidine ring, was achieved from trans-4-hydroxy-L-proline as a homochiral starting material using the diastereoselective Bucherer-Bergs reaction of(2S)-1-benzyl-2-[(diisopropylphosphonyl)methyl]-4-oxopyrrolidine 12.

  DOI：

  10.1016/0957-4166(95)00302-6

文献信息

• Synthesis of homochiral 4-amino-4-carboxy-2-phosphonomethylpyrrolidines via a diastereoselective bucherer-bergs reaction of 4-oxopyrrolidine derivative: Novel conformationally restricted AP 5 analogues
  作者：Ken-ichi Tanaka、Hirokazu Iwabuchi、Hiroyuki Sawanishi

  DOI：10.1016/0957-4166(95)00302-6

  日期：1995.9

  Asymmetric synthesis of 4-amino-4-carboxy-2-phosphonomethylpyrrolidines 1 and 2, which can be viewed as novel conformationally restricted analogues of 2-amino-5-phosphonopentanoic acid (AP 5) incorporated into the pyrrolidine ring, was achieved from trans-4-hydroxy-L-proline as a homochiral starting material using the diastereoselective Bucherer-Bergs reaction of(2S)-1-benzyl-2-[(diisopropylphosphonyl)methyl]-4-oxopyrrolidine 12.