6,7,9-trideoxy-6,9-(N-benzyloxycarbonylimino)-1,2:3,4-di-O-isopropylidene-8(S)-hydroxy-α-D-erythreo-D-galacto-non-1,5-pyranose | 947142-78-1

• 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: 6,7,9-trideoxy-6,9-(N-benzyloxycarbonylimino)-1,2:3,4-di-O-isopropylidene-8(S)-hydroxy-α-D-erythreo-D-galacto-non-1,5-pyranose
• CAS: 947142-78-1
• 化学式: C₂₃H₃₁NO₈
• 分子量: 449.501
• InChiKey: UXFSYPORMTWFAY-AKIVOZEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6,7,9-trideoxy-6,9-(N-benzyloxycarbonylimino)-1,2:3,4-di-O-isopropylidene-8(S)-hydroxy-α-D-erythreo-D-galacto-non-1,5-pyranose 在 palladium on activated charcoal 三氟乙酸 、 ammonium formate 作用下， 以 水 、 甲醇 为溶剂， 反应 5.5h， 以82%的产率得到(2S,6S,7R,8S,9R,9aR)-2,6,7,8,9-pentahydroxy-perhydro-4-azaazulene
  参考文献：
  名称：

  1,3-Dipolar cycloaddition reaction of a d-galactose derived nitrone with allyl alcohol: synthesis of polyhydroxylated perhydroazaazulene alkaloids

  摘要：

  Diastereofacial intermolecular 1,3-dipolar cycloaddition of D-galactose derived nitrone with allyl alcohol followed by tosylation afforded, in a 1:1 ratio endo- and exo-isooxazolidines 4a and 4b with complete diastereoselectivity at the nitrone carbon. The N-O bond reductive cleavage and S(N)2 displacement afforded the pyrrolidine ring with a galactose appendage that on acetonide cleavage and reductive amino-cyclization afforded pentahydroxylated perhydroazaazulenes 1a and 1b. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.012
• 作为产物：
  描述：

  (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide 在 palladium on activated charcoal 吡啶 、 copper diacetate 、 ammonium formate 、 碳酸氢钠 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 11.5h， 生成 6,7,9-trideoxy-6,9-(N-benzyloxycarbonylimino)-1,2:3,4-di-O-isopropylidene-8(S)-hydroxy-α-D-erythreo-D-galacto-non-1,5-pyranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition reaction of a d-galactose derived nitrone with allyl alcohol: synthesis of polyhydroxylated perhydroazaazulene alkaloids

  摘要：

  Diastereofacial intermolecular 1,3-dipolar cycloaddition of D-galactose derived nitrone with allyl alcohol followed by tosylation afforded, in a 1:1 ratio endo- and exo-isooxazolidines 4a and 4b with complete diastereoselectivity at the nitrone carbon. The N-O bond reductive cleavage and S(N)2 displacement afforded the pyrrolidine ring with a galactose appendage that on acetonide cleavage and reductive amino-cyclization afforded pentahydroxylated perhydroazaazulenes 1a and 1b. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.012