(3R,4R,5R,6R)-3,4,5,6-tetra-O-acetyl-oct-7-en-1-yne-3,4,5,6-tetrol | 697756-59-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4R,5R,6R)-3,4,5,6-tetra-O-acetyl-oct-7-en-1-yne-3,4,5,6-tetrol
• 英文别名: [(3R,4R,5R,6R)-4,5,6-triacetyloxyoct-1-en-7-yn-3-yl] acetate
• CAS: 697756-59-5
• 化学式: C₁₆H₂₀O₈
• 分子量: 340.33
• InChiKey: IBSKEMMILHRFQL-KLHDSHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R,6R)-3,4,5,6-tetra-O-acetyl-oct-7-en-1-yne-3,4,5,6-tetrol 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(3R,4R,5R,6R)-3,4,5,6-tetra-O-acetyl-1-vinylcyclohexene-3,4,5,6-tetrol
  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
• 作为产物：
  描述：

  6,7-dideoxy-D-manno-hept-6-ene-pyranose 在 吡啶 、 正丁基锂 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 12.67h， 生成 (3R,4R,5R,6R)-3,4,5,6-tetra-O-acetyl-oct-7-en-1-yne-3,4,5,6-tetrol
  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