(2R,4S)-1-(t-butoxycarbonyl)-4-{[(t-butyldimethyl)silyloxy]methyl}azetidine-2-methanol | 351075-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (2R,4S)-1-(t-butoxycarbonyl)-4-{[(t-butyldimethyl)silyloxy]methyl}azetidine-2-methanol
• 英文别名: cis-1-Boc-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-azetidine；tert-butyl (2S,4R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(hydroxymethyl)azetidine-1-carboxylate
• CAS: 351075-51-9
• 化学式: C₁₆H₃₃NO₄Si
• 分子量: 331.528
• InChiKey: ZHTYVWVJOUGBNM-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4S)-1-(t-butoxycarbonyl)-4-{[(t-butyldimethyl)silyloxy]methyl}azetidine-2-methanol 在 N-甲基吗啉 、 ruthenium trichloride 、 sodium periodate 、 草酰氯 、 碳酸氢钠 、 二甲基亚砜 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 23.28h， 生成 (S)-1-BOC-2-氮杂环丁烷甲醇
  参考文献：
  名称：

  Synthesis of chiral non-racemic azetidines by lipase-catalysed acetylations and their transformation into amino alcohols: precursors of chiral catalysts

  摘要：

  Azetidinic mono-acetate 7, diol 6b and di-acetate 10a were prepared with high e.e. using PPL-catalysed acetylations. The absolute configurations of all new enantioenriched compounds were assigned by chemical correlation with known compounds. Mono-acetate 7 was then transformed into 30, an amino alcohol of noteworthy potential interest since it represents an interesting precursor for chiral catalysts, such as 32. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00077-5
• 作为产物：
  描述：

  (2S,4R)-4-acetoxymethyl-1-benzylazetidine-2-methanol 在 palladium dihydroxide 咪唑 、 氢氧化钾 、 sodium hydroxide 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、506.62 kPa 条件下， 反应 53.0h， 生成 (2R,4S)-1-(t-butoxycarbonyl)-4-{[(t-butyldimethyl)silyloxy]methyl}azetidine-2-methanol
  参考文献：
  名称：

  Synthesis of chiral non-racemic azetidines by lipase-catalysed acetylations and their transformation into amino alcohols: precursors of chiral catalysts

  摘要：

  Azetidinic mono-acetate 7, diol 6b and di-acetate 10a were prepared with high e.e. using PPL-catalysed acetylations. The absolute configurations of all new enantioenriched compounds were assigned by chemical correlation with known compounds. Mono-acetate 7 was then transformed into 30, an amino alcohol of noteworthy potential interest since it represents an interesting precursor for chiral catalysts, such as 32. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00077-5