(2R,3S,6S)-<1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-piperidyl>propyl tosylate | 219715-86-3

• 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-phenylmethoxy-2-phenylmethoxymethyl-6-piperidyl>propyl tosylate
• 英文别名: 3-[(2S,5S,6R)-1-(4-methylphenyl)sulfonyl-5-phenylmethoxy-6-(phenylmethoxymethyl)piperidin-2-yl]propyl 4-methylbenzenesulfonate
• CAS: 219715-86-3
• 化学式: C₃₇H₄₃NO₇S₂
• 分子量: 677.883
• InChiKey: JZTPVVACGCJJSV-DLTAMOENSA-N

物化性质

• 沸点：
  775.932±70.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.296±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.21
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,6S)-<1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-piperidyl>propyl tosylate 在 palladium on activated charcoal dilithium tetrachlorocuprate 、 氨 、 氢气 、 sodium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 13.5h， 生成 (2R,3S,6S)-6-十二烷基-2-(羟甲基)哌啶-3-醇
  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
• 作为产物：
  描述：

  (2R,6S)-1,6-dihydro-1-tosyl-6-hydroxy-2-phenylmethoxymethyl-3(2H)-pyridinone 在 sodium hydroxide 、 sodium tetrahydroborate 、 dimethyl sulfide borane 、 4 A molecular sieve 、 三氟化硼乙醚 、 双氧水 、 四氯化钛 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.75h， 生成 (2R,3S,6S)-<1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-piperidyl>propyl tosylate
  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

• Asymmetric total synthesis of (+)-desoxoprosophylline
  作者：Cui-Fen Yang、Yi-Ming Xu、Li-Xin Liao、Wei-Shan Zhou

  DOI：10.1016/s0040-4039(98)02129-7

  日期：1998.12

  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.