2,3-di-O-benzyl-5-deoxy-1-dimethylphosphonyl-4-O-formyl-L-fucose | 266677-27-4

• 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: 2,3-di-O-benzyl-5-deoxy-1-dimethylphosphonyl-4-O-formyl-L-fucose
• 英文别名: [(2S,3R,4R,5R)-5-dimethoxyphosphoryl-5-hydroxy-3,4-bis(phenylmethoxy)pentan-2-yl] formate
• CAS: 266677-27-4
• 化学式: C₂₂H₂₉O₈P
• 分子量: 452.441
• InChiKey: XOLOAIGMPSEFON-ZHNGQKSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-5-deoxy-1-dimethylphosphonyl-4-O-formyl-L-fucose 在 palladium dihydroxide 三甲基溴硅烷 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 2.0h， 生成 L-fucophostone
  参考文献：
  名称：

  Synthesis of Glycophostones:  Cyclic Phosphonate Analogues of Biologically Relevant Sugars

  摘要：

  Analogues of L-fucose, N-acetyl-D-glucosamine, N-acetyl-D-mannosamine, and N-acetyl neuraminic acid in which the anomeric carbon atom was replaced by a phosphonyl group (phostones or cyclic phosphonates) were synthesized by stereocontrolled methods relying on the Abramov reaction.

  DOI：

  10.1021/jo991696l
• 作为产物：
  描述：

  3,4-di-O-benzyl-L-fucal 、 三甲氧基磷 在 二甲基硫 、 臭氧 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 以93 mg的产率得到2,3-di-O-benzyl-5-deoxy-1-dimethylphosphonyl-4-O-formyl-L-fucose
  参考文献：
  名称：

  Synthesis of Glycophostones:  Cyclic Phosphonate Analogues of Biologically Relevant Sugars

  摘要：

  Analogues of L-fucose, N-acetyl-D-glucosamine, N-acetyl-D-mannosamine, and N-acetyl neuraminic acid in which the anomeric carbon atom was replaced by a phosphonyl group (phostones or cyclic phosphonates) were synthesized by stereocontrolled methods relying on the Abramov reaction.

  DOI：

  10.1021/jo991696l

文献信息

• Synthesis of Glycophostones:  Cyclic Phosphonate Analogues of Biologically Relevant Sugars
  作者：Stephen Hanessian、Olivier Rogel

  DOI：10.1021/jo991696l

  日期：2000.5.1

  Analogues of L-fucose, N-acetyl-D-glucosamine, N-acetyl-D-mannosamine, and N-acetyl neuraminic acid in which the anomeric carbon atom was replaced by a phosphonyl group (phostones or cyclic phosphonates) were synthesized by stereocontrolled methods relying on the Abramov reaction.