tert-butyl (1R,2S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3,3-trifluoro-2-methylpropyl carbamate | 888725-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (1R,2S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3,3-trifluoro-2-methylpropyl carbamate
• 英文别名: tert-butyl N-[(1R,2S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,3,3-trifluoro-2-methylpropyl]carbamate
• CAS: 888725-61-9
• 化学式: C₁₄H₂₄F₃NO₄
• 分子量: 327.344
• InChiKey: ZUFVWOUVYHLSAC-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3,3-trifluoro-2-methylpropyl carbamate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以83%的产率得到tert-butyl (2S,3R,4S)-1,1,1-trifluoro-4,5-dihydroxy-2-methylpentan-3-ylcarbamate
  参考文献：
  名称：

  Indium-Mediated Diastereoselective Allylation of d- and l-Glyceraldimines with 4-Bromo-1,1,1-trifluoro-2-butene:  Highly Stereoselective Synthesis of 4,4,4-Trifluoroisoleucines and 4,4,4-Trifluorovaline

  摘要：

  A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4-trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4-bromo-1,1,1-trifluoro-2-butene 4 gave the desired homoallylic amine 8 in high diastereoselectivity (> 95% de) with moderate yield. The Cbz-protected (2R,3S)-4,4,4-trifluoroisoleucine 14 and Boc-protected (2R,3S)-4,4,4-trifluorovaline 21 were then readily prepared from 8. In addition, following the same procedure, Cbz-protected (2S,3R)-4,4,4-trifluoroisoleucine 28, the enantiomer of 14, was prepared starting from (S)-N-benzyl-2,3-O-isopropylideneglyceraldimine 24.

  DOI：

  10.1021/jo0601157
• 作为产物：
  描述：

  (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 indium 、 氢气 、 三正丁基氢锡 、 臭氧 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 41.0h， 生成 tert-butyl (1R,2S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3,3-trifluoro-2-methylpropyl carbamate
  参考文献：
  名称：

  Indium-Mediated Diastereoselective Allylation of d- and l-Glyceraldimines with 4-Bromo-1,1,1-trifluoro-2-butene:  Highly Stereoselective Synthesis of 4,4,4-Trifluoroisoleucines and 4,4,4-Trifluorovaline

  摘要：

  A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4-trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4-bromo-1,1,1-trifluoro-2-butene 4 gave the desired homoallylic amine 8 in high diastereoselectivity (> 95% de) with moderate yield. The Cbz-protected (2R,3S)-4,4,4-trifluoroisoleucine 14 and Boc-protected (2R,3S)-4,4,4-trifluorovaline 21 were then readily prepared from 8. In addition, following the same procedure, Cbz-protected (2S,3R)-4,4,4-trifluoroisoleucine 28, the enantiomer of 14, was prepared starting from (S)-N-benzyl-2,3-O-isopropylideneglyceraldimine 24.

  DOI：

  10.1021/jo0601157

文献信息

• Indium-Mediated Diastereoselective Allylation of <scp>d</scp>- and <scp>l</scp>-Glyceraldimines with 4-Bromo-1,1,1-trifluoro-2-butene:  Highly Stereoselective Synthesis of 4,4,4-Trifluoroisoleucines and 4,4,4-Trifluorovaline
  作者：Qi Chen、Xiao-Long Qiu、Feng-Ling Qing

  DOI：10.1021/jo0601157

  日期：2006.5.1

  A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4-trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4-bromo-1,1,1-trifluoro-2-butene 4 gave the desired homoallylic amine 8 in high diastereoselectivity (> 95% de) with moderate yield. The Cbz-protected (2R,3S)-4,4,4-trifluoroisoleucine 14 and Boc-protected (2R,3S)-4,4,4-trifluorovaline 21 were then readily prepared from 8. In addition, following the same procedure, Cbz-protected (2S,3R)-4,4,4-trifluoroisoleucine 28, the enantiomer of 14, was prepared starting from (S)-N-benzyl-2,3-O-isopropylideneglyceraldimine 24.