(4S,5S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-phenyl-1,3-oxazolidin-2-one | 131751-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-phenyl-1,3-oxazolidin-2-one
• CAS: 131751-46-7
• 化学式: C₁₆H₂₅NO₃Si
• 分子量: 307.465
• InChiKey: UEABAMGRGAEUGT-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-phenyl-1,3-oxazolidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 氢氟酸 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 64.0h， 生成 L-threo-2-amino-3-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：

  [(1S,2S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid benzyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(4S,5S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  The stereochemical outcome from mitsunobu couplings of vicinal, N-protected acyclic amino alcohols

  摘要：

  DOI：

  10.1016/s0040-4039(00)98043-2

文献信息

• The stereochemical outcome from mitsunobu couplings of vicinal, N-protected acyclic amino alcohols
  作者：Bruce H. Lipshutz、Todd A. Miller

  DOI：10.1016/s0040-4039(00)98043-2

  日期：1990.1
• 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.