(4R,5S)-3-[(1R,2S,3S,4S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-trimethylsilanylethynyl-pentyl]-4,5-diphenyl-oxazolidin-2-one | 653591-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5S)-3-[(1R,2S,3S,4S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-trimethylsilanylethynyl-pentyl]-4,5-diphenyl-oxazolidin-2-one
• CAS: 653591-62-9
• 化学式: C₄₅H₅₇NO₆Si₂
• 分子量: 764.122
• InChiKey: GGWCMWSLRNLECE-CLXZVIBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.72
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-[(1R,2S,3S,4S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-trimethylsilanylethynyl-pentyl]-4,5-diphenyl-oxazolidin-2-one 在 palladium diacetate air 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以47%的产率得到(4R,5S)-3-[(2S,3R)-2-((1S,2S)-1,2-Bis-benzyloxy-3-hydroxy-propyl)-5-oxo-tetrahydro-furan-3-yl]-4,5-diphenyl-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of 1-Deoxy-d-galactohomonojirimycin via Enantiomerically Pure Allenylstannanes

  摘要：

  1-Deoxy-D-galactohomonojirimycin was synthesized in seven steps from optically pure allenylstannane 4 and L-lactate-derived aldehyde 5 in 48% overall yield. The key step was the Lewis acid catalyzed reaction of 4 and 5 to give the syn-amino alcohol in excellent yield and very high diastereoselectivity.

  DOI：

  10.1021/jo0303012
• 作为产物：
  描述：

  (2R,3S)-4-[tert-butyl(dimethyl)silyl]oxy-2,3-bis(phenylmethoxy)butanal 、 (4R,5S)-4,5-Diphenyl-3-(3-tributylstannanyl-3-trimethylsilanyl-propa-1,2-dienyl)-oxazolidin-2-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以90%的产率得到(4R,5S)-3-[(1R,2S,3S,4S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-trimethylsilanylethynyl-pentyl]-4,5-diphenyl-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of 1-Deoxy-d-galactohomonojirimycin via Enantiomerically Pure Allenylstannanes

  摘要：

  1-Deoxy-D-galactohomonojirimycin was synthesized in seven steps from optically pure allenylstannane 4 and L-lactate-derived aldehyde 5 in 48% overall yield. The key step was the Lewis acid catalyzed reaction of 4 and 5 to give the syn-amino alcohol in excellent yield and very high diastereoselectivity.

  DOI：

  10.1021/jo0303012