6-deoxy-6-ethylsorbose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-6-ethylsorbose
• 英文别名: (3R,4S,5R)-1,3,4,5-tetrahydroxyoctan-2-one
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: REZBCKCTJLFEPL-DTLFHODZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,1-dimethoxy-pentan-2-ol 、 dihydroxyacetone phosphate disodium salt 生成 6-deoxy-6-ethylfructose 、 6-deoxy-6-ethylsorbose
  参考文献：
  名称：

  Diastereoselectivity (enantioselectivity) of aldol condensations catalyzed by rabbit muscle aldolase at C-2 of RCHOHCHO if R has an appropriately placed negatively charged group

  摘要：

  D-Fructose 1,6-bis(phosphate) aldolase from rabbit muscle (RAMA, E.C. 4.1.2.13) catalyzes the aldol condensation between dihydroxyacetone phosphate (DHAP) and various aldehydes; the products are ketosugars with 3(S),4(R) stereochemistry. When racemic alpha-hydroxy aldehydes are condensed with DHAP, two diastereomeric products are formed. This paper demonstrates that RAMA can kinetically resolve alpha-hydroxy aldehydes with a negative charge removed four or five atoms from the aldehydic center. Kinetic resolution of either uncharged alpha-hydroxy aldehydes, or of alpha-hydroxy aldehydes with a negative charge removed three or seven atoms from the aldehydic carbon, is generally not as successful.

  DOI：

  10.1021/jo00059a047

文献信息

• Diastereoselectivity (enantioselectivity) of aldol condensations catalyzed by rabbit muscle aldolase at C-2 of RCHOHCHO if R has an appropriately placed negatively charged group
  作者：Watson J. Lees、George M. Whitesides

  DOI：10.1021/jo00059a047

  日期：1993.3

  D-Fructose 1,6-bis(phosphate) aldolase from rabbit muscle (RAMA, E.C. 4.1.2.13) catalyzes the aldol condensation between dihydroxyacetone phosphate (DHAP) and various aldehydes; the products are ketosugars with 3(S),4(R) stereochemistry. When racemic alpha-hydroxy aldehydes are condensed with DHAP, two diastereomeric products are formed. This paper demonstrates that RAMA can kinetically resolve alpha-hydroxy aldehydes with a negative charge removed four or five atoms from the aldehydic center. Kinetic resolution of either uncharged alpha-hydroxy aldehydes, or of alpha-hydroxy aldehydes with a negative charge removed three or seven atoms from the aldehydic carbon, is generally not as successful.