(4R,5R)-5-Phenyl-4-pyrrolidin-1-ylmethyl-oxazolidin-2-one | 218766-22-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (4R,5R)-5-Phenyl-4-pyrrolidin-1-ylmethyl-oxazolidin-2-one
• 英文别名: (4R,5R)-5-phenyl-4-(pyrrolidin-1-ylmethyl)-1,3-oxazolidin-2-one
• CAS: 218766-22-4
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: NAHJBVFNZDPTLS-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-Phenyl-4-pyrrolidin-1-ylmethyl-oxazolidin-2-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以80.7%的产率得到(1R,2R)-2-Amino-3-pyrrolidino-1-phenyl-1-propanol
  参考文献：
  名称：

  Glycosyltransferase Inhibitors:  Synthesis of d-threo-PDMP, l-threo-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from d- or l-Serine

  摘要：

  The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2-decanoylamino-3-N-morpholino-1- propanol (L-threo-PDMP) (la) from L-serine, and the enantiomer (1R,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (Ib) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the beta-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure Ib in high yield after six steps. Three other D-threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D-threo-PDPP (le). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.

  DOI：

  10.1021/jo980951j
• 作为产物：
  描述：

  (1R,2R)-2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-propan-1-ol 在 吡啶 、 氢氟酸 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 25.75h， 生成 (4R,5R)-5-Phenyl-4-pyrrolidin-1-ylmethyl-oxazolidin-2-one
  参考文献：
  名称：

  Glycosyltransferase Inhibitors:  Synthesis of d-threo-PDMP, l-threo-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from d- or l-Serine

  摘要：

  The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2-decanoylamino-3-N-morpholino-1- propanol (L-threo-PDMP) (la) from L-serine, and the enantiomer (1R,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (Ib) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the beta-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure Ib in high yield after six steps. Three other D-threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D-threo-PDPP (le). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.

  DOI：

  10.1021/jo980951j