(2R,3S,6R)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-(1-hydroxy-2-ethyl)piperidine | 249284-75-1

• 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-(1-hydroxy-2-ethyl)piperidine
• 英文别名: 2-[(2R,5S,6R)-1-(4-methylphenyl)sulfonyl-5-phenylmethoxy-6-(phenylmethoxymethyl)piperidin-2-yl]ethanol
• CAS: 249284-75-1
• 化学式: C₂₉H₃₅NO₅S
• 分子量: 509.667
• InChiKey: MVADVXWEEAIINF-CMYDWJSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,6R)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-(1-hydroxy-2-ethyl)piperidine 在 dilithium tetrachlorocuprate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.17h， 生成 (2R,3S,6S)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-<9-(2-ethyl-1,3-dioxol-2-yl)nonyl>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
• 作为产物：
  描述：

  (2R,3S,6S)-1-tosyl-3-phenylmethoxy-6-ethyloxy-2-phenylmethoxymethylpiperidine 在 sodium tetrahydroborate 、 二甲基硫 、 四氯化钛 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 (2R,3S,6R)-1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-(1-hydroxy-2-ethyl)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

• 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.