3,4-O-isopropylidene-1,2:5,6-dianhydro-D-iditol | 185450-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-O-isopropylidene-1,2:5,6-dianhydro-D-iditol
• 英文别名: (4S,5S)-2,2-dimethyl-4,5-bis[(2R)-oxiran-2-yl]-1,3-dioxolane
• CAS: 185450-02-6
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: TYISXKCAFNKLQV-NGJRWZKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-O-isopropylidene-1,2:5,6-dianhydro-D-iditol 在 二苯基磷酸 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 7.33h， 生成 2,5-diazido-2,5-dideoxy-3,4-O-isopropylidene-1,6-di-O-phenyl-L-mannitol
  参考文献：
  名称：

  Cyclic HIV-1 Protease Inhibitors Derived from Mannitol:  Synthesis, Inhibitory Potencies, and Computational Predictions of Binding Affinities

  摘要：

  Ten C-2-symmetric cyclic urea and sulfamide derivatives have been synthesized from L-mannonic gamma-lactone and D-mannitol. The results of experimental measurement of their inhibitory potencies against HIV-1 protease were compared to calculated free energies of binding derived from molecular dynamics (MD) simulations. The compounds were selected, firstly, to enable elucidation of the role of stereochemistry for binding affinity (1a-d) and, secondly, to allow evaluation of the effects of variation in the link to the P1 and P1' phenyl groups on affinity (la and 2-5). Thirdly, compounds with hydrogen bond-accepting or -donating groups attached to the phenyl groups in the P2 and P2' side chains (6 and 7) were selected. Binding free energies were estimated by a linear response method, whose predictive power for estimating binding affinities from MD simulations was demonstrated.

  DOI：

  10.1021/jm960728j
• 作为产物：
  描述：

  [(2S)-2-[(4R,5R)-5-[(1S)-2-benzoyloxy-1-(4-methylphenyl)sulfonyloxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(4-methylphenyl)sulfonyloxyethyl] benzoate 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 3,4-O-isopropylidene-1,2:5,6-dianhydro-D-iditol
  参考文献：
  名称：

  HIV-1 Protease Inhibitors Based on Acyclic Carbohydrates

  摘要：

  A series of acyclic Ct-symmetric HIV protease inhibitors readily accessible from D-mannitol have been developed. Several of the compounds synthesized showed significant in vitro activity against HIV-1 protease.

  DOI：

  10.1021/jo971562c