2-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonylamido]ethyl α-D-mannopyranoside | 1192215-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonylamido]ethyl α-D-mannopyranoside
• 英文别名: 2-(1-methyl-7-propan-2-ylazulen-4-yl)ethyl N-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]carbamate
• CAS: 1192215-19-2
• 化学式: C₂₅H₃₅NO₈
• 分子量: 477.555
• InChiKey: QFUPVZQZCYAEAQ-DJCPXJLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonylamido]ethyl α-D-mannopyranoside 、 乙硫醇 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.08h， 以72%的产率得到2-aminoethyl α-D-mannopyranoside
  参考文献：
  名称：

  Coloring Carbohydrates: Investigation of Azulene Derivatives as Blue Protecting Groups

  摘要：

  Coloring carbohydrate derivatives by a chromophore tag greatly facilitates all purification steps during a synthetic sequence, according to a methodology called "chromophore- supported purification" (CSP). Herein an Fmoc-analogous blue protective group for CSP is introduced, based on guaiazulene. Following a mechanistic rational, the synthesis and introduction of this new protecting group is shown, together with its removal under variable conditions and its application for the synthesis of glycoclusters of a glycopeptide and glycopeptoid type.

  DOI：

  10.1080/07328300903040214
• 作为产物：
  描述：

  2-(7-isopropyl-1-methylazulen-4-yl)ethyl N-succinimidyl carbonate 、 2-aminoethyl α-D-mannopyranoside 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到2-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonylamido]ethyl α-D-mannopyranoside
  参考文献：
  名称：

  Coloring Carbohydrates: Investigation of Azulene Derivatives as Blue Protecting Groups

  摘要：

  Coloring carbohydrate derivatives by a chromophore tag greatly facilitates all purification steps during a synthetic sequence, according to a methodology called "chromophore- supported purification" (CSP). Herein an Fmoc-analogous blue protective group for CSP is introduced, based on guaiazulene. Following a mechanistic rational, the synthesis and introduction of this new protecting group is shown, together with its removal under variable conditions and its application for the synthesis of glycoclusters of a glycopeptide and glycopeptoid type.

  DOI：

  10.1080/07328300903040214

文献信息

• Coloring Carbohydrates: Investigation of Azulene Derivatives as Blue Protecting Groups
  作者：Ingo B. Aumüller、Thisbe K. Lindhorst

  DOI：10.1080/07328300903040214

  日期：2009.7.29

  Coloring carbohydrate derivatives by a chromophore tag greatly facilitates all purification steps during a synthetic sequence, according to a methodology called "chromophore- supported purification" (CSP). Herein an Fmoc-analogous blue protective group for CSP is introduced, based on guaiazulene. Following a mechanistic rational, the synthesis and introduction of this new protecting group is shown, together with its removal under variable conditions and its application for the synthesis of glycoclusters of a glycopeptide and glycopeptoid type.