6-methyl-L-galacto-(2R)-methoxy-1,2λ⁵-oxaphosphorinan-2-one | 266677-31-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 6-methyl-L-galacto-(2R)-methoxy-1,2λ⁵-oxaphosphorinan-2-one
• 英文别名: (2R,3R,4R,5S,6S)-2-methoxy-6-methyl-2-oxo-1,2lambda5-oxaphosphinane-3,4,5-triol；(2R,3R,4R,5S,6S)-2-methoxy-6-methyl-2-oxo-1,2λ5-oxaphosphinane-3,4,5-triol
• CAS: 266677-31-0
• 化学式: C₆H₁₃O₆P
• 分子量: 212.139
• InChiKey: NBOKBUBJBJROAD-YBYIVDNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 6-methyl-L-galacto-(2R)-methoxy-1,2λ⁵-oxaphosphorinan-2-one 在 三氟化硼乙醚 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 以20 mg的产率得到3,4,5-tri-O-acetyl-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
• 作为产物：
  描述：

  2,3-di-O-benzyl-5-deoxy-1-dimethylphosphonyl-4-O-formyl-L-fucose 在 palladium dihydroxide 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 6-methyl-L-galacto-(2R)-methoxy-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.