benzyl N-[[5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)-2-nitrophenyl]methyl]-N-[2-(2-hydroxyethoxy)ethyl]carbamate | 1548722-88-8

• 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: benzyl N-[[5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)-2-nitrophenyl]methyl]-N-[2-(2-hydroxyethoxy)ethyl]carbamate
• CAS: 1548722-88-8
• 化学式: C₃₀H₂₇F₁₇N₂O₇
• 分子量: 850.526
• InChiKey: UGKBPWJUFPZUKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  56
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  benzyl N-[[5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)-2-nitrophenyl]methyl]-N-[2-(2-hydroxyethoxy)ethyl]carbamate 以 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(2-(((benzyloxy)carbonyl)amino)ethoxy)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines

  摘要：

  Two new fluorous photolabile-protecting groups (FNBC and FNB) and a new base-labile protecting group (FOC) for the masking of amines are reported. The protecting groups survive a wide range of common reaction conditions used in oligosaccharide synthesis and render the attached molecules amenable to fluorous solid-phase extraction (FSPE). A glycosyl acceptor containing the FNB group is shown to be useful in the synthesis of carbohydrates tagged with free deactivated secondary amines.

  DOI：

  10.1021/ol500023y
• 作为产物：
  描述：

  4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl methanesulfonate 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 benzyl N-[[5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)-2-nitrophenyl]methyl]-N-[2-(2-hydroxyethoxy)ethyl]carbamate
  参考文献：
  名称：

  Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines

  摘要：

  Two new fluorous photolabile-protecting groups (FNBC and FNB) and a new base-labile protecting group (FOC) for the masking of amines are reported. The protecting groups survive a wide range of common reaction conditions used in oligosaccharide synthesis and render the attached molecules amenable to fluorous solid-phase extraction (FSPE). A glycosyl acceptor containing the FNB group is shown to be useful in the synthesis of carbohydrates tagged with free deactivated secondary amines.

  DOI：

  10.1021/ol500023y

文献信息

• Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines
  作者：Rajarshi Roychoudhury、Nicola L. B. Pohl

  DOI：10.1021/ol500023y

  日期：2014.2.21

  Two new fluorous photolabile-protecting groups (FNBC and FNB) and a new base-labile protecting group (FOC) for the masking of amines are reported. The protecting groups survive a wide range of common reaction conditions used in oligosaccharide synthesis and render the attached molecules amenable to fluorous solid-phase extraction (FSPE). A glycosyl acceptor containing the FNB group is shown to be useful in the synthesis of carbohydrates tagged with free deactivated secondary amines.