(1R,2R)-2-Amino-1-phenyl-3-thiomorpholin-4-yl-propan-1-ol | 218766-24-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-2-Amino-1-phenyl-3-thiomorpholin-4-yl-propan-1-ol
• 英文别名: (1R,2R)-2-amino-1-phenyl-3-thiomorpholin-4-ylpropan-1-ol
• CAS: 218766-24-6
• 化学式: C₁₃H₂₀N₂OS
• 分子量: 252.381
• InChiKey: OJGNOMAEIDUTSN-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对硝基苯酚癸 、 (1R,2R)-2-Amino-1-phenyl-3-thiomorpholin-4-yl-propan-1-ol 在 1-羟基苯并三唑 作用下， 以 吡啶 为溶剂， 以81.3%的产率得到(1R,2R)-(+)-1-phenyl-2-decanoylamino-3-(N-thiomorpholino)-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：

  (4R,5R)-(+)-4-(4'-p-toluenesulfonyloxymethyl)-5-phenyloxazolidin-2-one 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 65.0h， 生成 (1R,2R)-2-Amino-1-phenyl-3-thiomorpholin-4-yl-propan-1-ol
  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

文献信息

• Glycosyltransferase Inhibitors:  Synthesis of <scp>d</scp>-<i>threo</i>-PDMP, <scp>l</scp>-<i>threo</i>-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from <scp>d</scp>- or <scp>l</scp>-Serine
  作者：Scott A. Mitchell、Bryan D. Oates、Hossein Razavi、Robin Polt

  DOI：10.1021/jo980951j

  日期：1998.11.1

  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.