(4S,5S)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-3-ethoxycarbonyl-5-methyl-4,5-dihydroisoxazole 2-oxide | 332080-28-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5S)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-3-ethoxycarbonyl-5-methyl-4,5-dihydroisoxazole 2-oxide
• 英文别名: ethyl (4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methyl-2-oxido-4H-1,2-oxazol-2-ium-3-carboxylate
• CAS: 332080-28-1
• 化学式: C₂₀H₄₁NO₆Si₂
• 分子量: 447.72
• InChiKey: UWTLVUDPMTYHQN-JXFKEZNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-3-ethoxycarbonyl-5-methyl-4,5-dihydroisoxazole 2-oxide 在 三甲氧基磷 作用下， 反应 5.0h， 以95%的产率得到(4S,5S)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-3-ethoxycarbonyl-5-methyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  One-Pot Direct Conversion of 2,3-Epoxy Alcohols into Enantiomerically Pure 4-Hydroxy-4,5-dihydroisoxazole 2-Oxides

  摘要：

  [GRAPHICS]A new methodology for the one-pot direct conversion of 2,3-epoxy alcohols into enantiomerically pure 4-hydroxy-4,5-dihydroisoxazole P-oxides 1 has been found. The reaction works at room temperature and can be run at the 5-10 g scale. The mixture of 4,5-cis and 4,5-trans isomers obtained can be separated as such or as the bis-TDS ethers, A preliminary example of reductive cleavage of 1 to the corresponding amino polyol is also reported.

  DOI：

  10.1021/ol0070379
• 作为产物：
  描述：

  4-hydroxy-5-hydroxymethyl-5-methyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (4R,5S)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-3-ethoxycarbonyl-5-methyl-4,5-dihydroisoxazole 2-oxide 、 (4S,5S)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-3-ethoxycarbonyl-5-methyl-4,5-dihydroisoxazole 2-oxide
  参考文献：
  名称：

  One-Pot Direct Conversion of 2,3-Epoxy Alcohols into Enantiomerically Pure 4-Hydroxy-4,5-dihydroisoxazole 2-Oxides

  摘要：

  [GRAPHICS]A new methodology for the one-pot direct conversion of 2,3-epoxy alcohols into enantiomerically pure 4-hydroxy-4,5-dihydroisoxazole P-oxides 1 has been found. The reaction works at room temperature and can be run at the 5-10 g scale. The mixture of 4,5-cis and 4,5-trans isomers obtained can be separated as such or as the bis-TDS ethers, A preliminary example of reductive cleavage of 1 to the corresponding amino polyol is also reported.

  DOI：

  10.1021/ol0070379

文献信息

• One-Pot Direct Conversion of 2,3-Epoxy Alcohols into Enantiomerically Pure 4-Hydroxy-4,5-dihydroisoxazole 2-Oxides
  作者：Emanuela Marotta、Laure Marie Micheloni、Noemi Scardovi、Paolo Righi

  DOI：10.1021/ol0070379

  日期：2001.3.1

  [GRAPHICS]A new methodology for the one-pot direct conversion of 2,3-epoxy alcohols into enantiomerically pure 4-hydroxy-4,5-dihydroisoxazole P-oxides 1 has been found. The reaction works at room temperature and can be run at the 5-10 g scale. The mixture of 4,5-cis and 4,5-trans isomers obtained can be separated as such or as the bis-TDS ethers, A preliminary example of reductive cleavage of 1 to the corresponding amino polyol is also reported.