tert-butyl 1-(2-(benzyloxy)-2-((3aR,5R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl)ethylamino)-3-methyl-1-oxobutan-2-ylcarbamate | 1379771-66-0

• 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: tert-butyl 1-(2-(benzyloxy)-2-((3aR,5R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl)ethylamino)-3-methyl-1-oxobutan-2-ylcarbamate
• CAS: 1379771-66-0
• 化学式: C₃₃H₄₆N₂O₈
• 分子量: 598.737
• InChiKey: VQAHTRMLCCFDEG-XHKXPCOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  113.58
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 tert-butyl 1-(2-(benzyloxy)-2-((3aR,5R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl)ethylamino)-3-methyl-1-oxobutan-2-ylcarbamate 在 三氟乙酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 水 、 甲醇 为溶剂， 反应 30.0h， 以48%的产率得到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 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 tert-butyl 1-(2-(benzyloxy)-2-((3aR,5R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl)ethylamino)-3-methyl-1-oxobutan-2-ylcarbamate
  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