(S)-lactaldehyde diethyl acetal | 136616-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-lactaldehyde diethyl acetal
• 英文别名: (2S)-1,1-diethoxypropan-2-ol
• CAS: 136616-73-4
• 化学式: C₇H₁₆O₃
• 分子量: 148.202
• InChiKey: SWJACVWAJZRNFO-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  10.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  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

文献信息

• Enantioselective hydrogenation of α-keto acetals with cinchona modified Pt catalyst
  作者：Martin Studer、Stefan Burkhardt、Hans-Ulrich Blaser

  DOI：10.1039/a905113i

  日期：——

  The enantioselective hydrogenation of a variety of α-keto acetals to the corresponding α-hydroxy acetals with Pt catalysts modified with cinchonidine derivatives is described with ees up to 97% and high reaction rates, and the influence of the substrate structure, the modifier and the reaction conditions (catalyst, solvent, temperature, pressure, modifier concentration) was investigated in some detail.

  该论文描述了用辛可尼丁衍生物修饰的铂催化剂将多种δ-酮乙缩醛对映体选择性氢化为相应的δ-羟基乙缩醛的过程，ees 高达 97%，反应速率高，并详细研究了底物结构、改性剂和反应条件（催化剂、溶剂、温度、压力、改性剂浓度）的影响。
• Production of optically active &agr;-hydroxyacetals
  申请人：Solvias AG

  公开号：US06660890B1

  公开（公告）日：2003-12-09

  A process for the heterogeneous and enantioselective hydrogenation of prochiral organic &agr;-keto compounds with platinum as the catalyst in the presence of a soluble or immobilized chiral aromatic nitrogen base with at least one basic nitrogen atom adjacent to stereogenic carbon atoms, whereby prochiral &agr;-ketoacetals are hydrogenated to optically active &agr;-hydroxyacetals.

  一种利用铂作为催化剂，在可溶或固定的手性芳香族氮碱存在下，对非对映异构的有机α-酮化合物进行杂化和对映选择性氢化的过程，该手性芳香族氮碱至少具有一个邻近立体异构碳原子的碱性氮原子，从而将非对映异构的α-酮缩醛氢化为光学活性的α-羟基缩醛。