(S)-lactaldehyde diethyl acetal O-acetate | 110773-72-3

• 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: (S)-lactaldehyde diethyl acetal O-acetate
• 英文别名: [(2S)-1,1-diethoxypropan-2-yl] acetate
• CAS: 110773-72-3
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: FBAPKJGIJAGTAM-ZETCQYMHSA-N

物化性质

• 沸点：
  229.8±20.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-lactaldehyde diethyl acetal O-acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (S)-lactaldehyde diethyl acetal
  参考文献：
  名称：

  Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars

  摘要：

  The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described. Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized. Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-omega-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose. Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose. Explanations for the stereoselectivity in the hydrogenolysis reactions were provided. Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases. A new empirical formula is developed to relate the inhibition constants and inhibitor binding for alpha- and beta-glucosidases.

  DOI：

  10.1021/jo00022a013
• 作为产物：
  描述：

  1,1-Diethoxypropan-2-yl acetate 以40%的产率得到(R)-lactaldehyde diethyl acetal
  参考文献：
  名称：

  Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars

  摘要：

  The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described. Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized. Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-omega-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose. Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose. Explanations for the stereoselectivity in the hydrogenolysis reactions were provided. Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases. A new empirical formula is developed to relate the inhibition constants and inhibitor binding for alpha- and beta-glucosidases.

  DOI：

  10.1021/jo00022a013

文献信息

• Asymmetric hydroformylation catalyzed by homogeneous and polymer-supported platinum complexes containing chiral phosphine ligands
  作者：Giovanni Parrinello、J. K. Stille

  DOI：10.1021/ja00257a036

  日期：1987.11

  Hydroformylation de styrene, isobutyl-4styrene, vinyl-2 et methoxy-6 vinyl-2-naphtalenes, acetate de vinyle, methacrylate de methyle, norbornene, en presence de chlorure stanneux et en presence d'orthoformiate de triethyle

  加氢甲酰化脱苯乙烯、异丁基-4 苯乙烯、乙烯基-2 和甲氧基-6 乙烯基-2-萘、乙酸乙烯酯、甲基丙烯酸酯、降冰片烯、氯化物 stanneux 和三乙基正甲酸酯的存在