(3R,4R,6S)-6-O-benzyl-1-N-butyl-3,4-dihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane | 1269439-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R,6S)-6-O-benzyl-1-N-butyl-3,4-dihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane
• CAS: 1269439-32-8
• 化学式: C₂₃H₃₇NO₅
• 分子量: 407.55
• InChiKey: GHLMALLBQMHIMO-NQQQLTFYSA-N

反应信息

• 作为反应物：
  描述：

  (3R,4R,6S)-6-O-benzyl-1-N-butyl-3,4-dihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane 在 盐酸 、 10% palladium on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 以88%的产率得到(3R,4R,6S)-1-N-butylazepane-3,4,6-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：

  (1S,4R,5R)-1-O-benzyl-4,5-O-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]-1,4,5-trihydroxy-2-cyclohexene 、 正丁胺 在 ruthenium trichloride 、 sodium periodate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 10.0h， 以40%的产率得到(3R,4R,6S)-6-O-benzyl-1-N-butyl-3,4-dihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane
  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