2-((4aR,6R,7R,8R,8aR)-7,8-Dihydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-N-octadecyl-acetamide | 288377-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((4aR,6R,7R,8R,8aR)-7,8-Dihydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-N-octadecyl-acetamide
• 英文别名: 2-[(4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-N-octadecylacetamide
• CAS: 288377-56-0
• 化学式: C₂₉H₅₅NO₆
• 分子量: 513.759
• InChiKey: RCRYKJXOSBPJTC-SUUNGRLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((4aR,6R,7R,8R,8aR)-7,8-Dihydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-N-octadecyl-acetamide 在 盐酸 作用下， 反应 1.0h， 以75%的产率得到N-Octadecyl-2-((2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetamide
  参考文献：
  名称：

  Synthesis of glycolipid analogues that disrupt binding of HIV-1 gp120 to galactosylceramide

  摘要：

  HIV-1 has been shown to infect CD3 negative cells by the binding of HIV gp120 to the glycolipid galactosylceramide (1) (GalCer). Several analogues of 1 were prepared to investigate the specific orientation of 1 in the membrane bilayer that is involved in gp120 binding. Interestingly, N-stearyl-1-deoxynojirimycin (8) displayed potent and specific affinity for gp 120 equal to that of 1, a finding that may shed light on the antiviral activity of N-butyl-1-deoxynojirimycin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00153-0
• 作为产物：
  描述：

  4,6-O-isopropylidene-D-galactopyranose 在 sodium methylate 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 2-((4aR,6R,7R,8R,8aR)-7,8-Dihydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-N-octadecyl-acetamide
  参考文献：
  名称：

  Synthesis of glycolipid analogues that disrupt binding of HIV-1 gp120 to galactosylceramide

  摘要：

  HIV-1 has been shown to infect CD3 negative cells by the binding of HIV gp120 to the glycolipid galactosylceramide (1) (GalCer). Several analogues of 1 were prepared to investigate the specific orientation of 1 in the membrane bilayer that is involved in gp120 binding. Interestingly, N-stearyl-1-deoxynojirimycin (8) displayed potent and specific affinity for gp 120 equal to that of 1, a finding that may shed light on the antiviral activity of N-butyl-1-deoxynojirimycin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00153-0

文献信息

• Synthesis of glycolipid analogues that disrupt binding of HIV-1 gp120 to galactosylceramide
  作者：Kevin T. Weber、Djilali Hammache、Jacques Fantini、Bruce Ganem

  DOI：10.1016/s0960-894x(00)00153-0

  日期：2000.5

  HIV-1 has been shown to infect CD3 negative cells by the binding of HIV gp120 to the glycolipid galactosylceramide (1) (GalCer). Several analogues of 1 were prepared to investigate the specific orientation of 1 in the membrane bilayer that is involved in gp120 binding. Interestingly, N-stearyl-1-deoxynojirimycin (8) displayed potent and specific affinity for gp 120 equal to that of 1, a finding that may shed light on the antiviral activity of N-butyl-1-deoxynojirimycin. (C) 2000 Elsevier Science Ltd. All rights reserved.