(2S,3R)-2,3-dihydroxybutanal | 5144-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-2,3-dihydroxybutanal
• CAS: 5144-78-5
• 化学式: C₄H₈O₃
• 分子量: 104.106
• InChiKey: DFFAMJFPVBTTBX-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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 、 (2S,3R)-2,3-dihydroxybutanal 在 盐酸 、 sodium hydroxide 、 Tris buffer 作用下， 生成 (3R,4S,5S,6R)-1,3,4,5,6-pentahydroxyheptan-2-one
  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-(1S,2R-dihydroxypropyl)-1,5-dihydro-3H-2,4-benzodioxepine 在 KCl-HCl buffer 作用下， 反应 10.0h， 生成 (2S,3R)-2,3-dihydroxybutanal
  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

• Enzymic Synthesis of L-Fucose and Analogs
  作者：Chi-Huey Wong、Ramon Alajarin、Francisco Moris-Varas、Olga Blanco、Eduardo Garcia-Junceda

  DOI：10.1021/jo00127a052

  日期：1995.11
• Sasaki, Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., 1958, vol. 42, p. 35
  作者：Sasaki

  DOI：——

  日期：——
• 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.