1-(cyclohexylmethyl)gulofuranose 2,3:5,6-diacetonide | 135902-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(cyclohexylmethyl)gulofuranose 2,3:5,6-diacetonide
• CAS: 135902-03-3
• 化学式: C₁₉H₃₂O₆
• 分子量: 356.459
• InChiKey: CVSQAYCBAJHKLU-ZSCFFZQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(cyclohexylmethyl)gulofuranose 2,3:5,6-diacetonide 在 palladium on activated charcoal N-乙基哌啶 、 lithium aluminium tetrahydride 、 ammonium formate 、 三甲基乙酰氯 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 57.67h， 生成 N-isovaleroyl-Phe-Nva <(2R,3R,4R,5R,6S)-1-cyclohexyl-3,4:6,7-di-O-isopropylidene-3,4,5,6,7-pentahydroxyhept-2-yl>amide
  参考文献：
  名称：

  Renin inhibitory pentols showing improved enteral bioavailability

  摘要：

  Incorporation of a C-terminal pentahydroxy functionality led to potent, low molecular weight hydrophilic renin inhibitors lacking the P1' side chain. As these compounds are easy to synthesize and have sufficient water solubility, they were chosen for further study. Compound 33 was transported across rabbit intestinal brush border membrane vesicles and yielded a hypotensive effect in sodium-depleted rhesus monkeys which lasted for 90 min when dosed at 2 mg/kg id.

  DOI：

  10.1021/jm00081a019
• 作为产物：
  描述：

  6-(2,2-二甲基-[1,3]二氧杂烷-4-基) -2,2-二甲基-二氢-呋喃并[3,4-d][1 ,3]二氧代-4-酮 、 溴甲基环己烷 在 magnesium 作用下， 生成 1-(cyclohexylmethyl)gulofuranose 2,3:5,6-diacetonide 、 (3R,4R,5R,6S)-1-cyclohexyl-2-(cyclohexylmethyl)-2,3,4,5,6,7-hexahydroxyheptane 3,4:6,7-diacetonide
  参考文献：
  名称：

  Renin inhibitory pentols showing improved enteral bioavailability

  摘要：

  Incorporation of a C-terminal pentahydroxy functionality led to potent, low molecular weight hydrophilic renin inhibitors lacking the P1' side chain. As these compounds are easy to synthesize and have sufficient water solubility, they were chosen for further study. Compound 33 was transported across rabbit intestinal brush border membrane vesicles and yielded a hypotensive effect in sodium-depleted rhesus monkeys which lasted for 90 min when dosed at 2 mg/kg id.

  DOI：

  10.1021/jm00081a019