(2R,6S)-1,6-dihydro-1-tosyl-6-ethoxy-2-phenylmethoxymethyl-3(2H)-pyridinone | 249284-71-7

• 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,6S)-1,6-dihydro-1-tosyl-6-ethoxy-2-phenylmethoxymethyl-3(2H)-pyridinone
• 英文别名: (2R,6S)-6-ethoxy-1-(4-methylphenyl)sulfonyl-2-(phenylmethoxymethyl)-2,6-dihydropyridin-3-one
• CAS: 249284-71-7
• 化学式: C₂₂H₂₅NO₅S
• 分子量: 415.51
• InChiKey: FPGHDTRNHOMUEX-IRLDBZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,6S)-1,6-dihydro-1-tosyl-6-ethoxy-2-phenylmethoxymethyl-3(2H)-pyridinone 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2R,3R,6S)-1-tosyl-6-ethoxy-2-phenylmethoxymethyl-1,2,3,6-tetrahydro-3-pyridyl acetate
  参考文献：
  名称：

  A new concise stereoselective method for the preparation of a β-hydroxyfurfurylamine derivative and synthesis of 1-deoxyazasugar isomers

  摘要：

  A new method to prepare a chiral building block, a beta-hydroxyfurfurylamine derivative, is achieved and 1-deoxyazasugar isomers are synthesized. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00382-1
• 作为产物：
  描述：

  (1S)-(2-furyl)ethane-1,2-diol 在 氢氧化钾 、 lithium aluminium tetrahydride 、 sodium azide 、 4 A molecular sieve 、 三氟化硼乙醚 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (2R,6S)-1,6-dihydro-1-tosyl-6-ethoxy-2-phenylmethoxymethyl-3(2H)-pyridinone
  参考文献：
  名称：

  A new concise stereoselective method for the preparation of a β-hydroxyfurfurylamine derivative and synthesis of 1-deoxyazasugar isomers

  摘要：

  A new method to prepare a chiral building block, a beta-hydroxyfurfurylamine derivative, is achieved and 1-deoxyazasugar isomers are synthesized. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00382-1

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.
• A new concise stereoselective method for the preparation of a β-hydroxyfurfurylamine derivative and synthesis of 1-deoxyazasugar isomers
  作者：Li-Xin Liao、Zhi-Min Wang、Hong-Xing Zhang、Wei-Shan Zhou

  DOI：10.1016/s0957-4166(99)00382-1

  日期：1999.9

  A new method to prepare a chiral building block, a beta-hydroxyfurfurylamine derivative, is achieved and 1-deoxyazasugar isomers are synthesized. (C) 1999 Elsevier Science Ltd. All rights reserved.