4-hydroxy-2-methylidene-5-oxo-pentanoic acid ethyl ester | 335317-55-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-hydroxy-2-methylidene-5-oxo-pentanoic acid ethyl ester
• 英文别名: ethyl 4-hydroxy-2-methylidene-5-oxopentanoate
• CAS: 335317-55-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: XWGKKBVWEAOTIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dihydroxyacetone phosphate disodium salt 、 4-hydroxy-2-methylidene-5-oxo-pentanoic acid ethyl ester 在 Dowex 50W-X₈ (H⁽¹⁺⁾ form) 、 rabbit muscle aldolase 、 sodium hydroxide 、 盐酸 、 acid phytase from Aspergillus ficuum 作用下， 以 水 为溶剂， 反应 92.0h， 以11%的产率得到(+)-6-deoxy-6-(1'-ethyl-oxycarbonyl-2'-vinyl)-(α,β)-D-fructofuranose
  参考文献：
  名称：

  Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues

  摘要：

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.069
• 作为产物：
  描述：

  2-(2-hydroxy-3,3-dimethoxy-propyl)acrylic acid ethyl ester 在 lithium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以34%的产率得到4-hydroxy-2-methylidene-5-oxo-pentanoic acid ethyl ester
  参考文献：
  名称：

  Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues

  摘要：

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.069