(S)-glycidaldehyde diethyl acetal | 128572-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (S)-glycidaldehyde diethyl acetal
• 英文别名: (2S)-2-(diethoxymethyl)oxirane
• CAS: 128572-83-8
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: QIQQWSQARNQPLP-LURJTMIESA-N

物化性质

• 沸点：
  190.3±20.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-glycidaldehyde diethyl acetal 在 lithium aluminium tetrahydride 、 水 作用下， 以 乙醚 为溶剂， 以89%的产率得到(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：

  (R)-2-acetoxy-3-chloropropanal diethyl acetal 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到(S)-glycidaldehyde diethyl acetal
  参考文献：
  名称：

  Enzymes in organic synthesis: synthesis of highly enantiomerically pure 1,2-epoxy aldehydes, epoxy alcohols, thiirane, aziridine, and glyceraldehyde 3-phosphate

  摘要：

  DOI：

  10.1021/jo00303a026

文献信息

• A new strategy for the synthesis of nucleoside analogs based on enzyme-catalyzed aldol reactions
  作者：Kevin K. C. Liu、Chi Huey Wong

  DOI：10.1021/jo00044a005

  日期：1992.8

  A new synthetic approach to nucleoside analogs based on enzyme-catalyzed aldol condensations has been demonstrated in the synthesis of 6-adenyl-6-deoxy-D-fructose and 6-adenyl-6-deoxy-L-sorbose.
• A New Route to Deoxythio sugars Based on Aldolases
  作者：Wen-Chih Chou、Lihren Chen、Jim-Min Fang、Chi-Huey Wong

  DOI：10.1021/ja00093a018

  日期：1994.7

  A new route to deoxythiosugars based on aldolases has been developed. Representative syntheses of several thioketoses and 1-deoxy-5-thio-D-glucose, 1-deoxy-5-thio-D-galactose, 1-deoxy-5-thio-L-altrose, 1-deoxy-5-thio-D-mannose, 1-deoxy-5-thio-L-mannose, and 2-deoxy-5-thio-D-ribose are illustrated with the use of fructose 1,6-diphosphate aldolase, fuculose 1-phosphate aldolase, rhamnulose 1-phosphate aldolase, and 2-deoxyribose 5-phosphate aldolase in reaction with an appropriate thioaldehyde, followed by reduction with triethylsilane in the presence of BF3.Et(2)O.
• PEDERSON, RICHARD L.;LIU, KEVIN K. -C.;RUTAN, JAMES F.;CHEN, LIHREN;WONG,+, J. ORG. CHEM., 55,(1990) N6, C. 4897-4901
  作者：PEDERSON, RICHARD L.、LIU, KEVIN K. -C.、RUTAN, JAMES F.、CHEN, LIHREN、WONG,+

  DOI：——

  日期：——
• Enzymes in organic synthesis: synthesis of highly enantiomerically pure 1,2-epoxy aldehydes, epoxy alcohols, thiirane, aziridine, and glyceraldehyde 3-phosphate
  作者：Richard L. Pederson、Kevin K. C. Liu、James F. Rutan、Lihren Chen、Chi Huey Wong

  DOI：10.1021/jo00303a026

  日期：1990.8
• Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars
  作者：Kevin K. C. Liu、Tetsuya Kajimoto、Lihren Chen、Ziyang Zhong、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/jo00022a013

  日期：1991.10

  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.