(4aR,5aR,8aR,9S,9aR)-9-Hydroxy-2,2-dimethyl-hexahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-7-one | 288377-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (4aR,5aR,8aR,9S,9aR)-9-Hydroxy-2,2-dimethyl-hexahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-7-one
• 英文别名: (1R,3R,7R,8S,9R)-8-hydroxy-11,11-dimethyl-2,6,10,12-tetraoxatricyclo[7.4.0.03,7]tridecan-5-one
• CAS: 288377-55-9
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: PUAQTGWUBUHSQQ-WVNOCHIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4aR,5aR,8aR,9S,9aR)-9-Hydroxy-2,2-dimethyl-hexahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-7-one 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 49.0h， 生成 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：

  (E)-(4S,5R)-4,5-Dihydroxy-5-((4S,5R)-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl)-pent-2-enoic acid methyl ester 在 sodium methylate 作用下， 以91%的产率得到(4aR,5aR,8aR,9S,9aR)-9-Hydroxy-2,2-dimethyl-hexahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-7-one
  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.