tert-butyl N-[(R)-[(4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(furan-2-yl)methyl]carbamate | 1174272-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[(R)-[(4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(furan-2-yl)methyl]carbamate
• CAS: 1174272-46-8
• 化学式: C₃₂H₄₃NO₆Si
• 分子量: 565.782
• InChiKey: IOIJXBLUVARXGB-HZFUHODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(R)-[(4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(furan-2-yl)methyl]carbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以93%的产率得到tert-butyl N-[(R)-furan-2-yl-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]carbamate
  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：

  tert-Butyl (1R,2S,3S)-4-tert-butyldiphenylsilyloxy-1-(2-furyl)-2,3-dihydroxybutylcarbamate 、 2,2-二甲氧基丙烷 在 camphor-10-sulfonic acid 作用下， 反应 24.0h， 以98%的产率得到tert-butyl N-[(R)-[(4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(furan-2-yl)methyl]carbamate
  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

文献信息

• An asymmetric approach to 5-O-carbamoyl-2-epi-polyoxamic acid and the total synthesis of 2′′-epi-polyoxin J
  作者：Yong-Chun Luo、Huan-Huan Zhang、Yao-Zong Liu、Rui-Ling Cheng、Peng-Fei Xu

  DOI：10.1016/j.tetasy.2009.03.033

  日期：2009.6

  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.