4,5-di-O-benzyl-6-methyl-L-galacto-(2R)-hydroxy-1,2λ⁵-oxaphosphorinan-2-one | 266677-33-2

• 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: 4,5-di-O-benzyl-6-methyl-L-galacto-(2R)-hydroxy-1,2λ⁵-oxaphosphorinan-2-one
• 英文别名: (3R,4R,5S,6S)-2-hydroxy-6-methyl-2-oxo-4,5-bis(phenylmethoxy)-1,2lambda5-oxaphosphinan-3-ol；(3R,4R,5S,6S)-2-hydroxy-6-methyl-2-oxo-4,5-bis(phenylmethoxy)-1,2λ5-oxaphosphinan-3-ol
• CAS: 266677-33-2
• 化学式: C₁₉H₂₃O₆P
• 分子量: 378.362
• InChiKey: LUXOOODHYVAYPN-JEDBISTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-di-O-benzyl-6-methyl-L-galacto-(2R)-hydroxy-1,2λ⁵-oxaphosphorinan-2-one 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到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：

  2,3-di-O-benzyl-5-deoxy-1-dimethylphosphonyl-4-O-formyl-L-fucose 在 三甲基溴硅烷 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4,5-di-O-benzyl-6-methyl-L-galacto-(2R)-hydroxy-1,2λ⁵-oxaphosphorinan-2-one
  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.