{(1S,3S,4S)-1-Benzyl-4-[(3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester | 186487-59-2

• 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: {(1S,3S,4S)-1-Benzyl-4-[(3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester
• 英文别名: ((1S,2S,4S)-1-Benzyl-4-tert-butoxycarbonylamino-2-hydroxy-5-phenyl-pentyl)-carbamic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester；tert-butyl N-[(2S,4S,5S)-5-[[(3aR,4S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl]oxycarbonylamino]-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• CAS: 186487-59-2
• 化学式: C₃₀H₄₀N₂O₇
• 分子量: 540.657
• InChiKey: VSLFBTCZQICUPX-NOIWARKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {(1S,3S,4S)-1-Benzyl-4-[(3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 [(1S,3S,4S)-1-Benzyl-4-(hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-3-hydroxy-5-phenyl-pentyl]-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester
  参考文献：
  名称：

  Evaluation of furofuran as a P2 ligand for symmetry-based HIV protease inhibitors

  摘要：

  The hexahydrofurofuranyloxy group was evaluated as a conformationally constrained Pt ligand for symmetry-based HIV protease inhibitors. A number of compounds showed nM level activity against HIV in MT4 cells and lower protein binding than the licensed protease inhibitor ritonavir. However, replacement of 5-thiazole of ritonavir with a furofuran caused a reduction of the bioavailability in vivo. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00528-8
• 作为产物：
  描述：

  (3S,3aR,6aS)-六氢呋喃并[2,3-b]呋喃-3-醇 在 N-甲基吗啉 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 {(1S,3S,4S)-1-Benzyl-4-[(3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Evaluation of furofuran as a P2 ligand for symmetry-based HIV protease inhibitors

  摘要：

  The hexahydrofurofuranyloxy group was evaluated as a conformationally constrained Pt ligand for symmetry-based HIV protease inhibitors. A number of compounds showed nM level activity against HIV in MT4 cells and lower protein binding than the licensed protease inhibitor ritonavir. However, replacement of 5-thiazole of ritonavir with a furofuran caused a reduction of the bioavailability in vivo. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00528-8

文献信息

• Evaluation of furofuran as a P2 ligand for symmetry-based HIV protease inhibitors
  作者：Xiaoqi Chen、Lin Li、Dale J. Kempf、Hing Sham、Norman E. Wideburg、Ayda Saldivar、Sudthida Vasavanonda、Kennan C. Marsh、Edith McDonald、Daniel W. Norbeck

  DOI：10.1016/s0960-894x(96)00528-8

  日期：1996.12

  The hexahydrofurofuranyloxy group was evaluated as a conformationally constrained Pt ligand for symmetry-based HIV protease inhibitors. A number of compounds showed nM level activity against HIV in MT4 cells and lower protein binding than the licensed protease inhibitor ritonavir. However, replacement of 5-thiazole of ritonavir with a furofuran caused a reduction of the bioavailability in vivo. Copyright (C) 1996 Elsevier Science Ltd