(2R,3S,6R)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-(2-propenyl)piperidine | 219715-83-0

• 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,6R)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-(2-propenyl)piperidine
• 英文别名: (2R,3S,6R)-1-(4-methylphenyl)sulfonyl-3-phenylmethoxy-2-(phenylmethoxymethyl)-6-prop-2-enylpiperidine
• CAS: 219715-83-0
• 化学式: C₃₀H₃₅NO₄S
• 分子量: 505.678
• InChiKey: VFNCSCARNNUOCZ-SHSRKSKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,6R)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-(2-propenyl)piperidine 在 palladium on activated charcoal sodium hydroxide 、 dilithium tetrachlorocuprate 、 dimethyl sulfide borane 、 氢气 、 双氧水 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 15.5h， 生成 (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
• 作为产物：
  描述：

  (2R,6S)-1,6-dihydro-1-tosyl-6-ethoxy-2-phenylmethoxymethyl-3(2H)-pyridinone 在 sodium tetrahydroborate 、 四氯化钛 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.75h， 生成 (2R,3S,6R)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-(2-propenyl)piperidine
  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.
• New concise asymmetric total synthesis of (+)-desoxoprosophylline and prosophylline
  作者：Cuifen Yang、Lixin Liao、Yiming Xu、Hongxing Zhang、Peng Xia、Weishan Zhou

  DOI：10.1016/s0957-4166(99)00239-6

  日期：1999.6

  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.