2,6,7-trideoxy-β-D-gluco-hept-6-ene-pyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6,7-trideoxy-β-D-gluco-hept-6-ene-pyranose
• 英文别名: (2R,4R,5S,6R)-6-ethenyloxane-2,4,5-triol
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: MERWPXNAUPGIJJ-GBNDHIKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 咪唑 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2,6,7-trideoxy-β-D-gluco-hept-6-ene-pyranose
  参考文献：
  名称：

  An Efficient Way to 1,7-Enynes and Ethyl 8-Yn-2-enoates from Aldohexoses and to Polyhydroxylated 1-Vinylcyclohexenes

  摘要：

  In this paper, we report the synthesis of carbohydrate-derived 1,7-enynes and subsequent metathesis to yield polyhydroxylated 1-vinylcyclohexenes. For example, we converted D-glucose 2 to the (6,7)dideoxy-D-gluco-hept-6-ene-pyranose 7, which led to the desired 1,7-enyne 16. The ring-closing metathesis of this 1,7-enyne 16 with the second generation Grubbs catalyst, under Mori's conditions, gave the corresponding polyhydroxylated 1-vinylcyclohexene 25 in 76% yield. The conversion of several aldohexoses into polyhydroxylated 1-vinylcyclohexenes was carried out with satisfying yields. We report also the synthesis of two carbohydrate-derived ethyl 8-yn-2-enoates from D-glucose derivatives.

  DOI：

  10.1021/jo035437e

文献信息

• An Efficient Way to 1,7-Enynes and Ethyl 8-Yn-2-enoates from Aldohexoses and to Polyhydroxylated 1-Vinylcyclohexenes
  作者：Franck Dolhem、Catherine Lièvre、Gilles Demailly

  DOI：10.1021/jo035437e

  日期：2004.5.1

  In this paper, we report the synthesis of carbohydrate-derived 1,7-enynes and subsequent metathesis to yield polyhydroxylated 1-vinylcyclohexenes. For example, we converted D-glucose 2 to the (6,7)dideoxy-D-gluco-hept-6-ene-pyranose 7, which led to the desired 1,7-enyne 16. The ring-closing metathesis of this 1,7-enyne 16 with the second generation Grubbs catalyst, under Mori's conditions, gave the corresponding polyhydroxylated 1-vinylcyclohexene 25 in 76% yield. The conversion of several aldohexoses into polyhydroxylated 1-vinylcyclohexenes was carried out with satisfying yields. We report also the synthesis of two carbohydrate-derived ethyl 8-yn-2-enoates from D-glucose derivatives.