1-ethynyl-[2,3:5,6]-di-O-isopropylidene-D-manno-furanose | 1190937-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-ethynyl-[2,3:5,6]-di-O-isopropylidene-D-manno-furanose
• 英文别名: (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-ethynyl-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ol
• CAS: 1190937-15-5
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: BYAHPXOZWOZPHG-NPIHSRPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-ethynyl-[2,3:5,6]-di-O-isopropylidene-D-manno-furanose 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以10%的产率得到
  参考文献：
  名称：

  An oxepinone route to carbohydrate based oxepines

  摘要：

  Oxepines are ring expanded analogs of glycals that can be used to prepare septanose carbohydrates. A route to carbohydrate based oxepines that utilizes oxepinones as a key intermediate has been developed. The oxepinone intermediates were prepared via an amine catalyzed cycloisomerization of furanose hemi-ketals. 1,2-Reduction of the oxepinones followed by acetylation provided the novel ring expanded enol ether products. Moderate diastereoselectivity was observed for the reduction based on the starting oxepinone. 1,4-Addition onto the oxepinones was also demonstrated. Overall, the syntheses reported here will allow for ready access to novel ring expanded carbohydrate analogs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.041
• 作为产物：
  描述：

  (3aS,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[(trimethylsilyl)ethynyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-ol 在 cesium fluoride 、 水 作用下， 以 水 、 乙腈 为溶剂， 以86%的产率得到1-ethynyl-[2,3:5,6]-di-O-isopropylidene-D-manno-furanose
  参考文献：
  名称：

  An oxepinone route to carbohydrate based oxepines

  摘要：

  Oxepines are ring expanded analogs of glycals that can be used to prepare septanose carbohydrates. A route to carbohydrate based oxepines that utilizes oxepinones as a key intermediate has been developed. The oxepinone intermediates were prepared via an amine catalyzed cycloisomerization of furanose hemi-ketals. 1,2-Reduction of the oxepinones followed by acetylation provided the novel ring expanded enol ether products. Moderate diastereoselectivity was observed for the reduction based on the starting oxepinone. 1,4-Addition onto the oxepinones was also demonstrated. Overall, the syntheses reported here will allow for ready access to novel ring expanded carbohydrate analogs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.041