((2R,3S,4S,5R)-2,5-Bis-benzyloxy-6-tert-butoxycarbonylamino-3,4-dihydroxy-hexyl)-carbamic acid tert-butyl ester | 180589-07-5

• 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: ((2R,3S,4S,5R)-2,5-Bis-benzyloxy-6-tert-butoxycarbonylamino-3,4-dihydroxy-hexyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2R,3S,4S,5R)-3,4-dihydroxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2,5-bis(phenylmethoxy)hexyl]carbamate
• CAS: 180589-07-5
• 化学式: C₃₀H₄₄N₂O₈
• 分子量: 560.688
• InChiKey: YPEVZHAOTLWQCX-VEYUFSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4S,5R)-2,5-Bis-benzyloxy-6-tert-butoxycarbonylamino-3,4-dihydroxy-hexyl)-carbamic acid tert-butyl ester 在 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 ((2S,4S,5R)-2,5-Bis-benzyloxy-6-tert-butoxycarbonylamino-4-hydroxy-hexyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis ofC₂Symmetric Potential Inhibitors of HIV-1 Protease From D-Mannitol

  摘要：

  D-Mannitol was used as precursor for the synthesis of acyclic C-2 symmetric potential HIV-1 protease inhibitors. The 1- and 6-hydroxy groups of D-mannitol were substituted by -NHBoc, -NHValZ, -SAr, -SOAr and -SO2Ar and the 2- and 5-hydroxy groups were benzylated. In some products one of the central hydroxyl groups was either inverted or deoxygenated. Despite a close structural similarity to previously published inhibitors none of the products showed significant inhibitory activity against HIV-1 protease.

  DOI：

  10.1080/07328309608005674
• 作为产物：
  描述：

  1,6-Diamino-2,5-di-O-benzyl-1,6-dideoxy-3,4-O-isopropylidene-D-mannitol 在 吡啶 、 盐酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 ((2R,3S,4S,5R)-2,5-Bis-benzyloxy-6-tert-butoxycarbonylamino-3,4-dihydroxy-hexyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis ofC₂Symmetric Potential Inhibitors of HIV-1 Protease From D-Mannitol

  摘要：

  D-Mannitol was used as precursor for the synthesis of acyclic C-2 symmetric potential HIV-1 protease inhibitors. The 1- and 6-hydroxy groups of D-mannitol were substituted by -NHBoc, -NHValZ, -SAr, -SOAr and -SO2Ar and the 2- and 5-hydroxy groups were benzylated. In some products one of the central hydroxyl groups was either inverted or deoxygenated. Despite a close structural similarity to previously published inhibitors none of the products showed significant inhibitory activity against HIV-1 protease.

  DOI：

  10.1080/07328309608005674