(1S,3R,4S,5R,6S,7S)-ethyl 4,5-bis(benzyloxy)-3-(hydroxymethyl)-2-oxabicyclo[4.1.0]heptane-7-carboxylate | 1170695-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4S,5R,6S,7S)-ethyl 4,5-bis(benzyloxy)-3-(hydroxymethyl)-2-oxabicyclo[4.1.0]heptane-7-carboxylate
• 英文别名: ethyl (1S,3R,4S,5R,6S,7S)-3-(hydroxymethyl)-4,5-bis(phenylmethoxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylate
• CAS: 1170695-82-5
• 化学式: C₂₄H₂₈O₆
• 分子量: 412.483
• InChiKey: AARGOPLSLRXOIF-UOKSHHMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,3R,4S,5R,6S,7S)-ethyl 4,5-bis(benzyloxy)-3-(hydroxymethyl)-2-oxabicyclo[4.1.0]heptane-7-carboxylate 在 迭氮酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以85%的产率得到(1S,3R,4S,5R,6S,7S)-ethyl 3-(azidomethyl)-4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylate
  参考文献：
  名称：

  Pyranocyclopropanyl sugar amino acids, a new class of constrained (di)peptide isosteres

  摘要：

  The design, synthesis and application of oxabicyclo[4.1.0]heptane amino acids as conformationally restricted sugar amino acid dipeptide isosteres are reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.009
• 作为产物：
  描述：

  ethyl (3R,4S,5R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,5-bis(phenylmethoxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以5.28 g的产率得到(1S,3R,4S,5R,6S,7S)-ethyl 4,5-bis(benzyloxy)-3-(hydroxymethyl)-2-oxabicyclo[4.1.0]heptane-7-carboxylate
  参考文献：
  名称：

  Pyranocyclopropanyl sugar amino acids, a new class of constrained (di)peptide isosteres

  摘要：

  The design, synthesis and application of oxabicyclo[4.1.0]heptane amino acids as conformationally restricted sugar amino acid dipeptide isosteres are reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.009

文献信息

• Pyranocyclopropanyl sugar amino acids, a new class of constrained (di)peptide isosteres
  作者：Martijn D.P. Risseeuw、Gijs A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1016/j.tetasy.2009.03.009

  日期：2009.5

  The design, synthesis and application of oxabicyclo[4.1.0]heptane amino acids as conformationally restricted sugar amino acid dipeptide isosteres are reported. (C) 2009 Elsevier Ltd. All rights reserved.