(2R,3S)-2,3-dihydroxy-3-phenylpropanal | 164105-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-2,3-dihydroxy-3-phenylpropanal
• CAS: 164105-13-9
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: PNMZJNFYCANKLJ-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-羟基-3-(磷酰氧基)-2-丙酮 、 (2R,3S)-2,3-dihydroxy-3-phenylpropanal 在 盐酸 、 sodium hydroxide 、 Tris buffer 作用下， 生成 6-phenyl-L-galacto-2-hexulose
  参考文献：
  名称：

  Synthesis of carbohydrates via tandem use of the osmium-catalyzed asymmetric dihydroxylation and enzyme-catalyzed aldol addition reactions

  摘要：

  A new strategy is described for the asymmetric synthesis of carbohydrate derivatives via the tandem use of the osmium-catalyzed asymmetric dihydroxylation (AD) and aldolase-catalyzed aldol addition reactions. Both D- and L-forms of fructose, 6-deoxy-galacto-2-heptulose, and 6-phenyl-galacto-2-hexulose were synthesized to illustrate this methodology.

  DOI：

  10.1021/ja00081a016
• 作为产物：
  描述：

  3-(3-phenyl-1-propenyl)-1,5-dihydro-3H-2,4-benzodioxepine 在 AD-mix-α 、 甲基磺酰胺 、 KCl-HCl buffer 作用下， 以 水 、 叔丁醇 为溶剂， 反应 58.0h， 生成 (2R,3S)-2,3-dihydroxy-3-phenylpropanal
  参考文献：
  名称：

  Synthesis of carbohydrates via tandem use of the osmium-catalyzed asymmetric dihydroxylation and enzyme-catalyzed aldol addition reactions

  摘要：

  A new strategy is described for the asymmetric synthesis of carbohydrate derivatives via the tandem use of the osmium-catalyzed asymmetric dihydroxylation (AD) and aldolase-catalyzed aldol addition reactions. Both D- and L-forms of fructose, 6-deoxy-galacto-2-heptulose, and 6-phenyl-galacto-2-hexulose were synthesized to illustrate this methodology.

  DOI：

  10.1021/ja00081a016

文献信息

• Recombinant 2-Deoxyribose-5-phosphate Aldolase in Organic Synthesis: Use of Sequential Two-Substrate and Three-Substrate Aldol Reactions
  作者：Chi-Huey Wong、Eduardo Garcia-Junceda、Lihren Chen、Olga Blanco、Harrie J. M. Gijsen、Darryl H. Steensma

  DOI：10.1021/ja00117a003

  日期：1995.3

  A new procedure has been developed for the large scale preparation of recombinant 2-deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4) from E. coli strain DH5 alpha (ATCC 86963). The enzyme was purified to homogeneity with an overall yield of 83% and in sufficient quantity to grow crystals suitable for X-ray diffraction studies. Using the sequential two- or three-substrate aldol reaction, DERA was applied to the synthesis of a variety of sugar analogs including deoxyriboses, 2-deoxyfucose analogs, dideoxyhexoses, trideoxyhexoses, deoxythiosugars, and C-13-substituted 2-deoxyribose-5-phosphate.
• Synthesis of carbohydrates via tandem use of the osmium-catalyzed asymmetric dihydroxylation and enzyme-catalyzed aldol addition reactions
  作者：Ian Henderson、K. Barry Sharpless、Chi Huey Wong

  DOI：10.1021/ja00081a016

  日期：1994.1

  A new strategy is described for the asymmetric synthesis of carbohydrate derivatives via the tandem use of the osmium-catalyzed asymmetric dihydroxylation (AD) and aldolase-catalyzed aldol addition reactions. Both D- and L-forms of fructose, 6-deoxy-galacto-2-heptulose, and 6-phenyl-galacto-2-hexulose were synthesized to illustrate this methodology.