(2R,3S,6S)-1-tosyl-3-hydroxy-2-hydroxymethyl-6-dodecylpiperidine | 219715-88-5

• 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: (2R,3S,6S)-1-tosyl-3-hydroxy-2-hydroxymethyl-6-dodecylpiperidine
• 英文别名: (2R,3S,6S)-6-dodecyl-2-(hydroxymethyl)-1-(4-methylphenyl)sulfonylpiperidin-3-ol
• CAS: 219715-88-5
• 化学式: C₂₅H₄₃NO₄S
• 分子量: 453.687
• InChiKey: GYTUFOMXMBSGHI-CAOCKLPOSA-N

物化性质

• 沸点：
  591.116±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.082±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  77.84
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,6S)-1-tosyl-3-hydroxy-2-hydroxymethyl-6-dodecylpiperidine 在 氨 、 sodium 作用下， 以46%的产率得到(2R,3S,6S)-6-十二烷基-2-(羟甲基)哌啶-3-醇
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-desoxoprosophylline

  摘要：

  Asymmetric total synthesis of (+)-desoxoprosophylline 2 from the alpha-furfuryl amine derivative 1 was accomplished via ten steps in an overall yield of 4%. The oxidation of 1 to dihydropyridone 3 was used as the key step. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02129-7
• 作为产物：
  描述：

  (2R,3S,6S)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-dodecylpiperidine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 7.5h， 以84%的产率得到(2R,3S,6S)-1-tosyl-3-hydroxy-2-hydroxymethyl-6-dodecylpiperidine
  参考文献：
  名称：

  New concise asymmetric total synthesis of (+)-desoxoprosophylline and prosophylline

  摘要：

  Asymmetric total syntheses of (+)-desoxoprosophylline 1 and prosophyiline 2 from 1-(alpha-furyl)-2 phenylmethoxy-N-tosylethylamine 3 were accomplished in 10 steps with an overall yield of 4% and in nine steps with an overall yield of 11%, respectively. The oxidation of 3 to dihydropyridone was used as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00239-6

文献信息

• Total Synthesis of Desoxoprosophylline:  Application of a Lactam-Derived Enol Triflate to Natural Product Synthesis
  作者：Tim Luker、Henk Hiemstra、W. Nico Speckamp

  DOI：10.1021/jo962347j

  日期：1997.5.1

  The total synthesis of desoxoprosophylline 1 from a piperidinone-derived enol triflate 8 has been realized and is one of the first applications of such lactam-derived triflates to natural product synthesis. Palladium-catalyzed methoxycarbonylation of 8 followed by 1,2-reduction and protection introduces the required C2 hydroxymethyl group, affording 10. The C3 hydroxy function is stereoselectively added by a novel N-tosylenamide hydroboration (de 88%), and the final C6 dodecyl chain is incorporated with complete stereocontrol, in a single step, via an N-tosyliminium ion-allylsilane coupling. Deprotection gives the natural product in an efficient 7.5% yield over nine steps.