5-fluoro-2,5-dideoxy-D-erythro-pentofuranose | 619332-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-fluoro-2,5-dideoxy-D-erythro-pentofuranose
• 英文别名: (4S,5S)-5-(fluoromethyl)oxolane-2,4-diol
• CAS: 619332-72-8
• 化学式: C₅H₉FO₃
• 分子量: 136.123
• InChiKey: OCXOWTUUTWBIDS-PYHARJCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-3-Fluoro-2-hydroxy-propionaldehyde 、 乙醛 在 乙二胺四乙酸 作用下， 以 水 为溶剂， 反应 48.0h， 以33%的产率得到5-fluoro-2,5-dideoxy-D-erythro-pentofuranose
  参考文献：
  名称：

  Deoxyribose 5-phosphate aldolase as a catalyst in asymmetric aldol condensation

  摘要：

  This paper describes the substrate specificity and synthetic utility of deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4). Eight donors and 20 acceptors have been tested as substrates. In addition to acetaldehyde, propanal, acetone, and fluoroacetone have been used to condense with a number of acceptor aldehydes. Thirteen aldol products have been prepared and characterized. A new stereogenic center with 3(S) configuration is formed when acetaldehyde, fluoroacetone, or acetone is used as a donor substrate. With propanal, two new stereogenic centers are formed with 2(R) and 3(S) configurations. The acceptor substrates have very little structural requirements. The 2-hydroxyaldehydes appear to react the fastest, and the D-isomers are better substrates than the L-isomers. The stereospecificity is absolute regardless of the chirality of 2-hydroxyaldehydes. The aldol reactions thus follow the Cram-Felkin mode of attack for D-substrates and anti-Cram-Felkin mode of attack for L-substrates.

  DOI：

  10.1021/ja00028a050

文献信息

• Deoxyribose 5-phosphate aldolase as a catalyst in asymmetric aldol condensation
  作者：Lihren Chen、David P. Dumas、Chi Huey Wong

  DOI：10.1021/ja00028a050

  日期：1992.1

  This paper describes the substrate specificity and synthetic utility of deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4). Eight donors and 20 acceptors have been tested as substrates. In addition to acetaldehyde, propanal, acetone, and fluoroacetone have been used to condense with a number of acceptor aldehydes. Thirteen aldol products have been prepared and characterized. A new stereogenic center with 3(S) configuration is formed when acetaldehyde, fluoroacetone, or acetone is used as a donor substrate. With propanal, two new stereogenic centers are formed with 2(R) and 3(S) configurations. The acceptor substrates have very little structural requirements. The 2-hydroxyaldehydes appear to react the fastest, and the D-isomers are better substrates than the L-isomers. The stereospecificity is absolute regardless of the chirality of 2-hydroxyaldehydes. The aldol reactions thus follow the Cram-Felkin mode of attack for D-substrates and anti-Cram-Felkin mode of attack for L-substrates.