(1R,2R)-2-amino-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol | 218766-11-1

• 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-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol
• 英文别名: (1R,2R)-2-amino-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-1-ol
• CAS: 218766-11-1
• 化学式: C₁₅H₂₇NO₂Si
• 分子量: 281.47
• InChiKey: RCEXJSANYAGMCX-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-amino-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol 在 吡啶 、 氢氧化钾 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 60.25h， 生成 (1R,2R)-2-amino-3-(N-morpholino)-1-phenylpropan-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
• 作为产物：
  描述：

  (1R,2R)-(-)-2-氨基-1-苯基-1,3-丙二醇 在 palladium on activated charcoal 咪唑 、 氢气 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0~30.0 ℃ 、517.12 kPa 条件下， 反应 12.5h， 生成 (1R,2R)-2-amino-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol
  参考文献：
  名称：

  Syntheses of 1,2-Amino Alcohols and Their Applications for Oxazaborolidine Catalyzed Enantioselective Reduction of Aromatic Ketones

  摘要：

  从 (1R,2R)-2-氨基-1-苯基丙烷-1,3-二醇出发，合成了六种新的手性 1,2 氨基醇衍生物。用这些氨基醇衍生物和 BH3-Me2S 原位生成的噁唑硼烷对芳基酮进行不对称还原，得到了具有良好收率和中高对映体过量的仲醇。

  DOI：

  10.1071/ch06412

文献信息

• Syntheses of 1,2-Amino Alcohols and Their Applications for Oxazaborolidine Catalyzed Enantioselective Reduction of Aromatic Ketones
  作者：Namdev S. Vatmurge、Braja G. Hazra、Vandana S. Pore

  DOI：10.1071/ch06412

  日期：——

  Six new chiral 1,2-amino alcohol derivatives have been synthesized starting from (1R,2R)-2-amino-1-phenylpropane-1,3-diol. Asymmetric reduction of aryl ketones with in-situ generated oxazaborolidine from these amino alcohol derivatives and BH3·Me2S afforded secondary alcohols with good yield and moderate to high enantiomeric excess.

  从 (1R,2R)-2-氨基-1-苯基丙烷-1,3-二醇出发，合成了六种新的手性 1,2 氨基醇衍生物。用这些氨基醇衍生物和 BH3-Me2S 原位生成的噁唑硼烷对芳基酮进行不对称还原，得到了具有良好收率和中高对映体过量的仲醇。
• 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.