2,3,4,5-tetra-O-benzyl-6-deoxy-6,6-(ethylene-1,2-dioxy)-D-glucose-propane-1,3-diyl dithioacetal | 1427016-60-1

• 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: 2,3,4,5-tetra-O-benzyl-6-deoxy-6,6-(ethylene-1,2-dioxy)-D-glucose-propane-1,3-diyl dithioacetal
• 英文别名: 2-[(1S,2S,3S,4R)-4-(1,3-dithian-2-yl)-1,2,3,4-tetrakis(phenylmethoxy)butyl]-1,3-dioxolane
• CAS: 1427016-60-1
• 化学式: C₃₉H₄₄O₆S₂
• 分子量: 672.907
• InChiKey: ASNDNFWDEPKGBY-MYOMABOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106
• 氢给体数：
  0
• 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-6,6-(ethylene-1,2-dioxy)-D-glucose-propane-1,3-diyl dithioacetal 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以84%的产率得到2,3,4,5-tetra-O-benzyl-6-deoxy-6,6-(ethylene-1,2-dioxy)-D-glucose
  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：

  D-glucose propane-1,3-diyl dithioacetal 在 甲醇 、 4-二甲氨基吡啶 、 草酰氯 、 硫酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 51.08h， 生成 2,3,4,5-tetra-O-benzyl-6-deoxy-6,6-(ethylene-1,2-dioxy)-D-glucose-propane-1,3-diyl dithioacetal
  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.