6-azido-1-fluoro-1,3,5-trideoxy-D-erythro-hexulose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-1-fluoro-1,3,5-trideoxy-D-erythro-hexulose
• 英文别名: (4S,5R)-5-(azidomethyl)-2-(fluoromethyl)oxolane-2,4-diol
• 化学式: C₆H₁₀FN₃O₃
• 分子量: 191.162
• InChiKey: WIMYWNXWZPUFGV-YRZWDFBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-azido-1-fluoro-1,3,5-trideoxy-D-erythro-hexulose 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以11%的产率得到6-fluoro-1,4,5,6-tetradeoxy-1,5-imino-D-lyxitol
  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
• 作为产物：
  描述：

  氟代丙酮 、 (2R)-3-叠氮基-2-羟基丙醛 以 水 为溶剂， 以70%的产率得到6-azido-1-fluoro-1,3,5-trideoxy-D-erythro-hexulose
  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