1,6-anhydro-3,4-dideoxy-2-C-ethynyl-β-D-threo-hexopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-anhydro-3,4-dideoxy-2-C-ethynyl-β-D-threo-hexopyranose
• 英文别名: (1S,4R,5R)-4-ethynyl-6,8-dioxabicyclo[3.2.1]octan-4-ol
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: XXRFAEWHLDWQRC-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3,4-dideoxy-2-C-ethynyl-β-D-threo-hexopyranose 、 苄基叠氮 在 copper(II) acetate monohydrate 作用下， 以 水 为溶剂， 反应 1.0h， 以84%的产率得到1,6-anhydro-3,4-dideoxy-2-C-(1-benzyl-1,2,3-triazol-4-yl)-β-D-threo-hexopyranose
  参考文献：
  名称：

  Levoglucosenone-derived precursors for the stereoselective synthesis of methylene-expanded analogues of C-nucleosides

  摘要：

  Simple chiral precursors for the preparation of methylene-expanded C-nucleosides were developed, using as key steps pyrolysis of cellulose to levoglucosenone followed by hydrogenation and introduction of vinyl and ethynyl fragments to the 2-position.

  DOI：

  10.1016/j.mencom.2015.01.016
• 作为产物：
  描述：

  左旋葡萄糖酮 在 溴乙烷 、 2% active carbon-supported palladium 、 氢气 、 magnesium 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 5.25h， 生成 1,6-anhydro-3,4-dideoxy-2-C-ethynyl-β-D-threo-hexopyranose 、 (1S,4S,5R)-4-ethynyl-6,8-dioxabicyclo[3.2.1]octan-4-ol
  参考文献：
  名称：

  Levoglucosenone-derived precursors for the stereoselective synthesis of methylene-expanded analogues of C-nucleosides

  摘要：

  Simple chiral precursors for the preparation of methylene-expanded C-nucleosides were developed, using as key steps pyrolysis of cellulose to levoglucosenone followed by hydrogenation and introduction of vinyl and ethynyl fragments to the 2-position.

  DOI：

  10.1016/j.mencom.2015.01.016

文献信息

• Levoglucosenone-derived precursors for the stereoselective synthesis of methylene-expanded analogues of C-nucleosides
  作者：Valery K. Brel、Aleksandr V. Samet、Leonid D. Konyushkin、Adam I. Stash、Vitaly K. Belsky、Victor V. Semenov

  DOI：10.1016/j.mencom.2015.01.016

  日期：2015.1

  Simple chiral precursors for the preparation of methylene-expanded C-nucleosides were developed, using as key steps pyrolysis of cellulose to levoglucosenone followed by hydrogenation and introduction of vinyl and ethynyl fragments to the 2-position.