Diazo-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethyl ester | 509085-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Diazo-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethyl ester
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl 2-diazoacetate
• CAS: 509085-97-6
• 化学式: C₃₄H₄₂N₂O₇Si
• 分子量: 618.802
• InChiKey: UVMVNUPJPCBADW-BRAMSPLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Diazo-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethyl ester 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以45%的产率得到
  参考文献：
  名称：

  Catalytic conversions of diazosugars

  摘要：

  Catalytic diazo decomposition chemistry was explored with novel diazoacetate functionalized carbohydrates. In both glucose and galactose derivatives, aromatic cycloadditions with the benzyl protecting groups proved to be most favorable reactions. Replacing the benzyl groups by methoxy groups in the glucose system led to formation of 'carbene dimers'. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02407-3
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 Diazo-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Catalytic conversions of diazosugars

  摘要：

  Catalytic diazo decomposition chemistry was explored with novel diazoacetate functionalized carbohydrates. In both glucose and galactose derivatives, aromatic cycloadditions with the benzyl protecting groups proved to be most favorable reactions. Replacing the benzyl groups by methoxy groups in the glucose system led to formation of 'carbene dimers'. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02407-3

文献信息

• Catalytic conversions of diazosugars
  作者：Hilbert M. Branderhorst、Johan Kemmink、Rob M.J. Liskamp、Roland J. Pieters

  DOI：10.1016/s0040-4039(02)02407-3

  日期：2002.12

  Catalytic diazo decomposition chemistry was explored with novel diazoacetate functionalized carbohydrates. In both glucose and galactose derivatives, aromatic cycloadditions with the benzyl protecting groups proved to be most favorable reactions. Replacing the benzyl groups by methoxy groups in the glucose system led to formation of 'carbene dimers'. (C) 2002 Elsevier Science Ltd. All rights reserved.