2,3,4,5-tetra-O-benzyl-6-deoxy-6-hydroxylamino-D-glucose ethylene acetal | 1427016-57-6

• 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: 2,3,4,5-tetra-O-benzyl-6-deoxy-6-hydroxylamino-D-glucose ethylene acetal
• 英文别名: N-((2R,3R,4S,5R)-2,3,4,5-Tetrakis(benzyloxy)-5-(1,3-dioxolan-2-yl)pentyl)hydroxylamine；N-[(2R,3R,4S,5R)-5-(1,3-dioxolan-2-yl)-2,3,4,5-tetrakis(phenylmethoxy)pentyl]hydroxylamine
• CAS: 1427016-57-6
• 化学式: C₃₆H₄₁NO₇
• 分子量: 599.724
• InChiKey: LASCIDODOWFZMZ-NDLNHBFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-benzyl-6-deoxy-6-hydroxylamino-D-glucose ethylene acetal 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到(3S,4R,5R,6R)-3,4,5,6-tetrakis(benzyloxy)-3,4,5,6-tetrahydro-7H-azepine 1-oxide
  参考文献：
  名称：

  General Synthesis of Sugar-Derived Azepane Nitrones: Precursors of Azepane Iminosugars

  摘要：

  A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.

  DOI：

  10.1021/jo400130p
• 作为产物：
  描述：

  2,3,4,5-tetra-O-benzyl-6-O-trityl-D-glucose propane-1,3-diyldithioacetal 在 盐酸 、 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 硫酸 、 盐酸羟胺 、 sodium cyanoborohydride 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 5.58h， 生成 2,3,4,5-tetra-O-benzyl-6-deoxy-6-hydroxylamino-D-glucose ethylene acetal
  参考文献：
  名称：

  General Synthesis of Sugar-Derived Azepane Nitrones: Precursors of Azepane Iminosugars

  摘要：

  A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.

  DOI：

  10.1021/jo400130p

文献信息

• General Synthesis of Sugar-Derived Azepane Nitrones: Precursors of Azepane Iminosugars
  作者：Wen-Bo Zhao、Shinpei Nakagawa、Atsushi Kato、Isao Adachi、Yue-Mei Jia、Xiang-Guo Hu、George W. J. Fleet、Francis X. Wilson、Graeme Horne、Akihide Yoshihara、Ken Izumori、Chu-Yi Yu

  DOI：10.1021/jo400130p

  日期：2013.4.5

  A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.