(R)-N-[1'-(2-Furyl)-2'-benzyloxyethyl]toluene-p-sulfonamide | 219715-78-3

• 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: (R)-N-[1'-(2-Furyl)-2'-benzyloxyethyl]toluene-p-sulfonamide
• 英文别名: (R)-1-(α-furyl)-2-phenylmethoxy-N-tosylethylamine；1-(α-furyl)-2-phenylmethoxy-N-tosylethylamine；N-[(1R)-1-(furan-2-yl)-2-phenylmethoxyethyl]-4-methylbenzenesulfonamide
• CAS: 219715-78-3
• 化学式: C₂₀H₂₁NO₄S
• 分子量: 371.457
• InChiKey: PNXVIGVVANLDBE-LJQANCHMSA-N

物化性质

• 沸点：
  498.3±55.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-N-[1'-(2-Furyl)-2'-benzyloxyethyl]toluene-p-sulfonamide 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 4 A molecular sieve 、 三氟化硼乙醚 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 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 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 (R)-N-[1'-(2-Furyl)-2'-benzyloxyethyl]toluene-p-sulfonamide
  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

• Chirally templated boronic acid Mannich reaction in the synthesis of optically active α-amino acids
  作者：Gordon S. Currie、Michael G. B. Drew、Laurence M. Harwood、David J. Hughes、Richard W. A. Luke、Richard J. Vickers

  DOI：10.1039/b003067h

  日期：——

  Adducts from diastereoselective Mannich-type reactions of aldehydes, 2-furylboronic acid and the chiral amine template (S)-5-phenylmorpholin-2-one, have been used in the synthesis of a series of enantiomerically pure D-α-amino acids.

  非对映选择性曼尼希型反应的加合物 醛类， 2-呋喃基硼酸 和手性 胺模板（S）-5-苯基吗啉-2-酮已用于合成一系列对映体纯的D -α-氨基酸。
• 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.
• 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.