(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 | 288377-54-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (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
• 英文别名: methyl (E,4S,5R)-4,5-dihydroxy-5-[(4S,5R)-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl]pent-2-enoate
• CAS: 288377-54-8
• 化学式: C₁₂H₂₀O₇
• 分子量: 276.287
• InChiKey: XHLKBBBDEWHMLU-JPZSDXHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4,6-O-isopropylidene-D-galactopyranose 、 甲氧羰基亚甲基三苯基正膦 生成 (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 、 (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
  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