(1R,2R,3R)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-5-butyl-3-O-methoxymethyl-4-cyclohexene-1,2,3-triol | 1269439-08-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3R)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-5-butyl-3-O-methoxymethyl-4-cyclohexene-1,2,3-triol
• CAS: 1269439-08-8
• 化学式: C₁₈H₃₂O₆
• 分子量: 344.448
• InChiKey: FBBFSXJYCWOURF-DZVNLGKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-5-butyl-3-O-methoxymethyl-4-cyclohexene-1,2,3-triol 在 盐酸 、 potassium permanganate 、 10% palladium on activated carbon 、 氢气 、 magnesium sulfate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 10.0h， 生成 、 (3R,4S,5R,7R)-7-butylazepane-3,4,5-triol
  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 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 生成 (1R,2R,3R)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-5-butyl-3-O-methoxymethyl-4-cyclohexene-1,2,3-triol
  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