(2S,3R,4R,5S)-2,5-Bis-azidomethyl-3,4-bis-benzyloxy-tetrahydro-furan | 323580-61-6

• 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)-2,5-Bis-azidomethyl-3,4-bis-benzyloxy-tetrahydro-furan
• 英文别名: (2S,3R,4R,5S)-2,5-bis(azidomethyl)-3,4-bis(phenylmethoxy)oxolane
• CAS: 323580-61-6
• 化学式: C₂₀H₂₂N₆O₃
• 分子量: 394.433
• InChiKey: ZXWDAHAULKLYKH-VNTMZGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S)-2,5-Bis-azidomethyl-3,4-bis-benzyloxy-tetrahydro-furan 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 tert-butyl N-[(2S)-1-[[(2S)-1-[[(2S,3S,4S,5S)-3,4-dihydroxy-5-[[[(2S)-2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]-3-phenylpropanoyl]amino]methyl]oxolan-2-yl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
  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 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3R,4R,5S)-2,5-Bis-azidomethyl-3,4-bis-benzyloxy-tetrahydro-furan
  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

文献信息

• 2,5-Anhydro sugar diacid and 2,5-anhydro sugar diamine based C2 symmetric peptidomimetics as potential HIV-1 protease inhibitors
  作者：T.K. Chakraborty、Subhash Ghosh、M.H.V. Ramana Rao、A.C. Kunwar、H. Cho、A.K. Ghosh

  DOI：10.1016/s0040-4039(00)01803-7

  日期：2000.12

  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.