tert-butyl (1R,2S,3S)-1-(2-furyl)-2,3,4-trihydroxybutylcarbamate | 1174272-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: tert-butyl (1R,2S,3S)-1-(2-furyl)-2,3,4-trihydroxybutylcarbamate
• 英文别名: tert-butyl N-[(1R,2S,3S)-1-(furan-2-yl)-2,3,4-trihydroxybutyl]carbamate
• CAS: 1174272-44-6
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: BXHQOGRGZMNBGN-INTQDDNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2S,3S)-1-(2-furyl)-2,3,4-trihydroxybutylcarbamate 、 叔丁基二苯基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以88%的产率得到tert-Butyl (1R,2S,3S)-4-tert-butyldiphenylsilyloxy-1-(2-furyl)-2,3-dihydroxybutylcarbamate
  参考文献：
  名称：

  An asymmetric approach to 5-O-carbamoyl-2-epi-polyoxamic acid and the total synthesis of 2′′-epi-polyoxin J

  摘要：

  A stereospecific synthetic approach to 5-O-carbamoyl-2-epi-polyoxamic acid has been developed. The asymmetric nucleophilic addition of 2-lithiofuran to a tert-butanesulfinyl imine was employed as the key step to construct the C-2 stereocenter and 2 ''-epi-polyoxin J has been synthesized for the first time. Significantly, the synthesis provides a facile method for the large scale and stereoselective preparation of 5-O-carbamoyl-2-epi-polyoxamic acid and some related diastereoisomers of polyoxins and its analogues because of its simple operation, excellent yield, and high stereoselectivity. This will be convenient for research of the polyoxins' structure-activity relationship and to search for more potent and effective anti-candidal agents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.033
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以241 mg的产率得到tert-butyl (1R,2S,3S)-1-(2-furyl)-2,3,4-trihydroxybutylcarbamate
  参考文献：
  名称：

  An asymmetric approach to 5-O-carbamoyl-2-epi-polyoxamic acid and the total synthesis of 2′′-epi-polyoxin J

  摘要：

  A stereospecific synthetic approach to 5-O-carbamoyl-2-epi-polyoxamic acid has been developed. The asymmetric nucleophilic addition of 2-lithiofuran to a tert-butanesulfinyl imine was employed as the key step to construct the C-2 stereocenter and 2 ''-epi-polyoxin J has been synthesized for the first time. Significantly, the synthesis provides a facile method for the large scale and stereoselective preparation of 5-O-carbamoyl-2-epi-polyoxamic acid and some related diastereoisomers of polyoxins and its analogues because of its simple operation, excellent yield, and high stereoselectivity. This will be convenient for research of the polyoxins' structure-activity relationship and to search for more potent and effective anti-candidal agents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.033