(4S,5R)-1-tert-butoxycarbonyl-5-(tert-butoxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)piperidin-2-one | 880548-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (4S,5R)-1-tert-butoxycarbonyl-5-(tert-butoxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)piperidin-2-one
• 英文别名: tert-butyl (4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxopiperidine-1-carboxylate
• CAS: 880548-63-0
• 化学式: C₃₁H₄₄N₂O₆Si
• 分子量: 568.786
• InChiKey: PHLNCTBNBJJQEL-RPBOFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1-tert-butoxycarbonyl-5-(tert-butoxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)piperidin-2-one 在 四丁基氟化铵 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 31.0h， 生成 (2S,4S,5R)-1-tert-butoxycarbonyl-5-(tert-butoxycarbonylamino)-2-hydroxymethyl-4-hydroxypiperidine
  参考文献：
  名称：

  A Stereocontrolled Formal Asymmetric Synthesis of Pseudodistomin C

  摘要：

  An efficient and stereocontrolled formal asymmetric synthesis of pseudodistomin C has been achieved by employing intramolecular transamidation reaction, exo-methylenation, and highly stercoselective hydroboration. The resulting 2-hydroxymethylpiperidine derivative (15) was further converted into the key intermediate (2) for the synthesis of pseudodistomin C.

  DOI：

  10.3987/com-05-10586
• 作为产物：
  描述：

  (4S,5R)-5-(tert-butoxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)piperidin-2-one 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(4S,5R)-1-tert-butoxycarbonyl-5-(tert-butoxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)piperidin-2-one
  参考文献：
  名称：

  A Stereocontrolled Formal Asymmetric Synthesis of Pseudodistomin C

  摘要：

  An efficient and stereocontrolled formal asymmetric synthesis of pseudodistomin C has been achieved by employing intramolecular transamidation reaction, exo-methylenation, and highly stercoselective hydroboration. The resulting 2-hydroxymethylpiperidine derivative (15) was further converted into the key intermediate (2) for the synthesis of pseudodistomin C.

  DOI：

  10.3987/com-05-10586

文献信息

• A Stereocontrolled Formal Asymmetric Synthesis of Pseudodistomin C
  作者：Ken-ichi Tanaka、Takuya Maesoba、Hiroyuki Sawanishi

  DOI：10.3987/com-05-10586

  日期：——

  An efficient and stereocontrolled formal asymmetric synthesis of pseudodistomin C has been achieved by employing intramolecular transamidation reaction, exo-methylenation, and highly stercoselective hydroboration. The resulting 2-hydroxymethylpiperidine derivative (15) was further converted into the key intermediate (2) for the synthesis of pseudodistomin C.