1,2-O-isopropylidene-3,5-di-O-benzyl-6-azido-α-D-allofuranose | 1379771-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-isopropylidene-3,5-di-O-benzyl-6-azido-α-D-allofuranose
• 英文别名: (3aR,5R,6R,6aR)-5-[(1R)-2-azido-1-phenylmethoxyethyl]-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 1379771-63-7
• 化学式: C₂₃H₂₇N₃O₅
• 分子量: 425.484
• InChiKey: CGKKLCAOMMBMCN-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3,5-di-O-benzyl-6-azido-α-D-allofuranose 在 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 33.0h， 生成 tert-butyl (6R,7R,8R,9S)-6,7,8,9-tetrahydroxy-2-isopropyl-3-oxo-1,4-diazecane-1-carboxylate
  参考文献：
  名称：

  Sugar–amino acid cyclic conjugates as novel conformationally constrained hydroxyethylamine transition-state isosteres

  摘要：

  Hydroxyethylamine (HEA) isosteres have previously been shown to display a multitude of biomedical applications. In fact, the first protease inhibitor, saquinavir is an HEA based peptidomimetic. Herein we describe an easy-to-operate synthetic route to a series of carbohydrate-based conformationally constrained hydroxyethylamine (HEA) isosteres featuring amino acid side chains, starting from D-glucose. This class of novel sugar-amino acid-tethered conformationally restricted HEA systems may have bearing in practical application, particularly in the development of conformationally restricted protease inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.086
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 sodium tetrahydroborate 、 sodium azide 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1,2-O-isopropylidene-3,5-di-O-benzyl-6-azido-α-D-allofuranose
  参考文献：
  名称：

  Sugar–amino acid cyclic conjugates as novel conformationally constrained hydroxyethylamine transition-state isosteres

  摘要：

  Hydroxyethylamine (HEA) isosteres have previously been shown to display a multitude of biomedical applications. In fact, the first protease inhibitor, saquinavir is an HEA based peptidomimetic. Herein we describe an easy-to-operate synthetic route to a series of carbohydrate-based conformationally constrained hydroxyethylamine (HEA) isosteres featuring amino acid side chains, starting from D-glucose. This class of novel sugar-amino acid-tethered conformationally restricted HEA systems may have bearing in practical application, particularly in the development of conformationally restricted protease inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.086