(+/-1)-(2-furan-2-yl-2-hydroxyethyl)carbamic acid benzyl ester | 383416-19-1

• 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: (+/-1)-(2-furan-2-yl-2-hydroxyethyl)carbamic acid benzyl ester
• 英文别名: (2-furan-2-yl-2-hydroxy-ethyl)-carbamic acid benzyl ester；benzyl N-[2-(furan-2-yl)-2-hydroxyethyl]carbamate
• CAS: 383416-19-1
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: AYUPQWPFXWLSIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  71.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-1)-(2-furan-2-yl-2-hydroxyethyl)carbamic acid benzyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到(2-furan-2-yl-2-oxo-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of N-Cbz-Protected 6-Amino-6-deoxymannose, -talose, and -gulose

  摘要：

  The enantioselective synthesis of three 6-amino-6-deoxy sugars has been achieved in six to eight steps from furfural. A sequence of diastereoselective oxidation and reduction reactions produced Cbz-protected 6-aminomannose from furfuryl alcohol 3. The incorporation of a Mitsunobu reaction into the reaction sequence allows for the selective synthesis of both N-Cbz-protected 6-aminotalose and 6-aminogulose. The overall procedure allows for the synthesis of either enantiomer of these three aminosugars. [reaction: see text]

  DOI：

  10.1021/ol016743m
• 作为产物：
  描述：

  1-(呋喃-2-基)-2-硝基乙醇 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 48.0h， 生成 (+/-1)-(2-furan-2-yl-2-hydroxyethyl)carbamic acid benzyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of N-Cbz-Protected 6-Amino-6-deoxymannose, -talose, and -gulose

  摘要：

  The enantioselective synthesis of three 6-amino-6-deoxy sugars has been achieved in six to eight steps from furfural. A sequence of diastereoselective oxidation and reduction reactions produced Cbz-protected 6-aminomannose from furfuryl alcohol 3. The incorporation of a Mitsunobu reaction into the reaction sequence allows for the selective synthesis of both N-Cbz-protected 6-aminotalose and 6-aminogulose. The overall procedure allows for the synthesis of either enantiomer of these three aminosugars. [reaction: see text]

  DOI：

  10.1021/ol016743m

文献信息

• Enantioselective Synthesis of <i>N</i>-Cbz-Protected 6-Amino-6-deoxymannose, -talose, and -gulose
  作者：Michael H. Haukaas、George A. O'Doherty

  DOI：10.1021/ol016743m

  日期：2001.11.1

  The enantioselective synthesis of three 6-amino-6-deoxy sugars has been achieved in six to eight steps from furfural. A sequence of diastereoselective oxidation and reduction reactions produced Cbz-protected 6-aminomannose from furfuryl alcohol 3. The incorporation of a Mitsunobu reaction into the reaction sequence allows for the selective synthesis of both N-Cbz-protected 6-aminotalose and 6-aminogulose. The overall procedure allows for the synthesis of either enantiomer of these three aminosugars. [reaction: see text]
• De Novo Asymmetric Approaches to 2-Amino-N-(benzyloxycarbonyl)-1-(2’-furyl)ethanol and 2-Amino-N-(tert-butoxycarbonyl)-1-(2’-furyl)ethanol
  作者：George A. O'Doherty、Michael H. Haukaas、Miaosheng Li、Alexey M. Starosotnikov、George A. O’Doherty

  DOI：10.3987/com-08-s(n)119

  日期：——