[(2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-ylmethyl]-carbamic acid tert-butyl ester | 323580-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-ylmethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[[(2S,3R,4R,5S)-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl]carbamate
• CAS: 323580-63-8
• 化学式: C₃₀H₄₂N₂O₇
• 分子量: 542.673
• InChiKey: PSKBPWLGUNSVQU-QEGGNFSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-ylmethyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S,3R,4R,5S)-5-(aminomethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanamine
  参考文献：
  名称：

  2,5-Anhydro sugar diacid and 2,5-anhydro sugar diamine based C2 symmetric peptidomimetics as potential HIV-1 protease inhibitors

  摘要：

  Conformationally constrained molecular frameworks of the 2,5-anhydro sugar diacid (9) and 2,5-anhydro sugar diamines (10, 11) were used to construct architecturally beautiful novel C-2 symmetric peptidomimetics 1-8. Although none of these compounds showed any significant HIV-I protease inhibitory activity, further refinements in design may lead to protease inhibitors based on these rigid carbohydrate-derived scaffolds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01803-7
• 作为产物：
  描述：

  2,5-anhydro-3,4-di-O-benzyl-L-iditol 在 4-二甲氨基吡啶 、 sodium azide 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-ylmethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  2,5-Anhydro sugar diacid and 2,5-anhydro sugar diamine based C2 symmetric peptidomimetics as potential HIV-1 protease inhibitors

  摘要：

  Conformationally constrained molecular frameworks of the 2,5-anhydro sugar diacid (9) and 2,5-anhydro sugar diamines (10, 11) were used to construct architecturally beautiful novel C-2 symmetric peptidomimetics 1-8. Although none of these compounds showed any significant HIV-I protease inhibitory activity, further refinements in design may lead to protease inhibitors based on these rigid carbohydrate-derived scaffolds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01803-7