Ethyl 2,3-dideoxy-2-methylidene-D-altro-octulonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2,3-dideoxy-2-methylidene-D-altro-octulonate
• 英文别名: ethyl (4R,5S,6R,7R)-4,5,6,7,8-pentahydroxy-2-methylideneoctanoate
• 化学式: C₁₁H₂₀O₇
• 分子量: 264.276
• InChiKey: GRDXUMPLWYFWGI-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 2,3-dideoxy-2-methylidene-D-altro-octulonate 在 二甲基硫 、 臭氧 作用下， 生成 Ethyl 3-deoxy-D-altro-oct-2-ulopyranosonate
  参考文献：
  名称：

  Tin- and indium-mediated allylation in aqueous media: application to unprotected carbohydrates

  摘要：

  The convenient and efficient indium- and tin-mediated allylation method for extending the carbon chain of unprotected carbohydrates is illustrated by preparation of 4-6 and 9-10. Various 2-deoxyaldoses can be synthesized by the allylation of aldoses. Indium-mediated reactions between ethyl 2-(bromomethyl)acrylate and aldoses provide access to 2-keto-3-deoxyulosonic acids. These reactions are diastereoselective; the major product contains a threo relationship between the newly generated hydroxyl group and the C-2 hydroxyl group of the starting carbohydrate. Results obtained from reactions involving authentic organotin and organoindium reagents and from the corresponding heterogeneous reactions are similar.

  DOI：

  10.1021/jo00072a038
• 作为产物：
  描述：

  D-核糖 、 2-溴甲基丙烯酸乙酯 在 indium 作用下， 以 乙醇 为溶剂， 以89%的产率得到Ethyl 2,3-dideoxy-2-methylidene-D-altro-octulonate
  参考文献：
  名称：

  Tin- and indium-mediated allylation in aqueous media: application to unprotected carbohydrates

  摘要：

  The convenient and efficient indium- and tin-mediated allylation method for extending the carbon chain of unprotected carbohydrates is illustrated by preparation of 4-6 and 9-10. Various 2-deoxyaldoses can be synthesized by the allylation of aldoses. Indium-mediated reactions between ethyl 2-(bromomethyl)acrylate and aldoses provide access to 2-keto-3-deoxyulosonic acids. These reactions are diastereoselective; the major product contains a threo relationship between the newly generated hydroxyl group and the C-2 hydroxyl group of the starting carbohydrate. Results obtained from reactions involving authentic organotin and organoindium reagents and from the corresponding heterogeneous reactions are similar.

  DOI：

  10.1021/jo00072a038

文献信息

• Tin- and indium-mediated allylation in aqueous media: application to unprotected carbohydrates
  作者：Enoch Kim、Dana M. Gordon、Walther Schmid、George M. Whitesides

  DOI：10.1021/jo00072a038

  日期：1993.9

  The convenient and efficient indium- and tin-mediated allylation method for extending the carbon chain of unprotected carbohydrates is illustrated by preparation of 4-6 and 9-10. Various 2-deoxyaldoses can be synthesized by the allylation of aldoses. Indium-mediated reactions between ethyl 2-(bromomethyl)acrylate and aldoses provide access to 2-keto-3-deoxyulosonic acids. These reactions are diastereoselective; the major product contains a threo relationship between the newly generated hydroxyl group and the C-2 hydroxyl group of the starting carbohydrate. Results obtained from reactions involving authentic organotin and organoindium reagents and from the corresponding heterogeneous reactions are similar.