N-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonyl]-N-{[2-(α-D-mannopyranosyloxy)ethyl]carbamoylmethyl}glycine methyl ester | 1192215-26-1

• 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: N-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonyl]-N-{[2-(α-D-mannopyranosyloxy)ethyl]carbamoylmethyl}glycine methyl ester
• CAS: 1192215-26-1
• 化学式: C₃₀H₄₂N₂O₁₁
• 分子量: 606.67
• InChiKey: FUJAWYBTIQLHQR-BSNVCIOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  184.32
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonyl]-N-{[2-(α-D-mannopyranosyloxy)ethyl]carbamoylmethyl}glycine methyl ester 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 以78%的产率得到N-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonyl]-N-{[2-(α-D-mannopyranosyloxy)ethyl]carbamoylmethyl}glycine
  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：

  N-[2-(7-isopropyl-1-methylazulen-4-yl)ethoxycarbonyl]iminodiacetic acid monomethyl ester 、 2-aminoethyl α-D-mannopyranoside 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到N-[2-(7-isopropyl-1-methyl-azulen-4-yl)ethoxycarbonyl]-N-{[2-(α-D-mannopyranosyloxy)ethyl]carbamoylmethyl}glycine methyl ester
  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