(2S,3S,4aR,5R,8aR)-7-butyl-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-ol | 1269439-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4aR,5R,8aR)-7-butyl-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-ol
• CAS: 1269439-14-6
• 化学式: C₁₆H₂₈O₅
• 分子量: 300.395
• InChiKey: PWBCIUXFKXBMKE-SUJAAXHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4aR,5R,8aR)-7-butyl-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-ol 在 4-二甲氨基吡啶 、 potassium permanganate 、 magnesium sulfate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors

  摘要：

  An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from D-(-)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against beta-galactosidase (IC50 = 3 mu M). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.014
• 作为产物：
  描述：

  (5R,6S)-5,6-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-3-butyl-cyclohex-2-enone 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 水 为溶剂， 以71%的产率得到(2S,3S,4aR,5R,8aR)-7-butyl-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-ol
  参考文献：
  名称：

  Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors

  摘要：

  An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from D-(-)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against beta-galactosidase (IC50 = 3 mu M). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.014