benzyl 4-(tri-O-benzyl-α-L-fucopyranosyl)-3-hydroxybutanoate | 1169517-46-7

• 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 4-(tri-O-benzyl-α-L-fucopyranosyl)-3-hydroxybutanoate
• 英文别名: benzyl 3-hydroxy-4-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]butanoate
• CAS: 1169517-46-7
• 化学式: C₃₈H₄₂O₇
• 分子量: 610.747
• InChiKey: KIVPZPHTTDEUIV-OLDAKQODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 4-(tri-O-benzyl-α-L-fucopyranosyl)-3-hydroxybutanoate 在 palladium dihydroxide 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以93%的产率得到4-(α-L-fucopyranosyl)-3-hydroxybutanoic acid
  参考文献：
  名称：

  Solid-phase supported mimic of GDP-l-galactose

  摘要：

  A C-glycoside mimetic of L-galactose 1-diphosphate, a potential ligand of GDP-L-galactose hydrolase, an enzyme involved in the biosynthesis of vitamin C, has been designed, stereoselectively synthesised by C-allylation of tribenzylated L-fucose, by periodate-osmium tetroxide degradation of the double bond, by condensation of the obtained aldehydes with benzylacetate and by deprotection. The obtained mimetic was linked to a sepharose resin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.005
• 作为产物：
  描述：

  乙酸苄酯 、 2-(tri-O-benzyl-α-L-fucopyranosyl)-acetaldehyde 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到benzyl 4-(tri-O-benzyl-α-L-fucopyranosyl)-3-hydroxybutanoate
  参考文献：
  名称：

  Solid-phase supported mimic of GDP-l-galactose

  摘要：

  A C-glycoside mimetic of L-galactose 1-diphosphate, a potential ligand of GDP-L-galactose hydrolase, an enzyme involved in the biosynthesis of vitamin C, has been designed, stereoselectively synthesised by C-allylation of tribenzylated L-fucose, by periodate-osmium tetroxide degradation of the double bond, by condensation of the obtained aldehydes with benzylacetate and by deprotection. The obtained mimetic was linked to a sepharose resin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.005

文献信息

• Solid-phase supported mimic of GDP-l-galactose
  作者：Barbara La Ferla、Laura Russo、Cristina Airoldi、Francesco Nicotra

  DOI：10.1016/j.tetasy.2009.03.005

  日期：2009.5

  A C-glycoside mimetic of L-galactose 1-diphosphate, a potential ligand of GDP-L-galactose hydrolase, an enzyme involved in the biosynthesis of vitamin C, has been designed, stereoselectively synthesised by C-allylation of tribenzylated L-fucose, by periodate-osmium tetroxide degradation of the double bond, by condensation of the obtained aldehydes with benzylacetate and by deprotection. The obtained mimetic was linked to a sepharose resin. (C) 2009 Elsevier Ltd. All rights reserved.