2-((S)-2-hydroxy-2-((4S,5S)-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl)ethyl)isoindoline-1,3-dione | 850426-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((S)-2-hydroxy-2-((4S,5S)-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl)ethyl)isoindoline-1,3-dione
• 英文别名: 2-[(2S)-2-hydroxy-2-[(4S,5S)-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]isoindole-1,3-dione
• CAS: 850426-77-6
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: DRVBPTBRZCXUOB-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((S)-2-hydroxy-2-((4S,5S)-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl)ethyl)isoindoline-1,3-dione 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Mimicking Dihydroxy Acetone Phosphate-Utilizing Aldolases through Organocatalysis:  A Facile Route to Carbohydrates and Aminosugars

  摘要：

  A practical and environmentally friendly organocatalytic strategy designed to mimic the DHAP aldolases has been developed and shown to be effective in the preparation of carbohydrates and aminosugars. (S)-Proline and (S)-2-pyrrolidine-tetrazole catalyzed the aldol reaction between dihydroxy acetone variants such as 1,3-dioxan-5-one and 2,2-dimethyl-1,3-dioxan-5-one with aldehydes to give the corresponding polyols in good yields with very high ees.

  DOI：

  10.1021/ol0502533
• 作为产物：
  描述：

  苯二甲酰亚氨基乙醛 在 L-Selectride 、 L-脯氨酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 2-((S)-2-hydroxy-2-((4S,5S)-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl)ethyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Dihydroxyacetone Variants in the Organocatalytic Construction of Carbohydrates:  Mimicking Tagatose and Fuculose Aldolases

  摘要：

  Dihydroxyacetone variants have been explored as donors in organocatalytic aldol reactions with various aldehyde and ketone acceptors. The protected form of dihydroxyacetone that was chosen for in-depth study was 2,2-dimethyl-1,3-dioxan-5-one, 1. Among the catalysts surveyed here, proline proved to be superior in terms of yield and stereoselectivities in the construction of various carbohydrate scaffolds. In a fashion analogous to aldolase enzymes, the de novo preparation of L-ribulose, L-lyxose, D-ribose, D-tagatose, 1-amino-1-deoxy-D-lyxitol, and other carbohydrates was accomplished via the use of 1 and proline. In reactions using 2,2-dimethyl-1,3-dioxan-5-one 1 as a donor, (S)-proline can be used as a functional mimic of tagatose aldolase, whereas (R)-proline can be regarded as an organocatalytic mimic of fuculose aldolase.

  DOI：

  10.1021/jo0602017

文献信息

• Mimicking Dihydroxy Acetone Phosphate-Utilizing Aldolases through Organocatalysis:  A Facile Route to Carbohydrates and Aminosugars
  作者：Jeff T. Suri、Dhevalapally B. Ramachary、Carlos F. Barbas

  DOI：10.1021/ol0502533

  日期：2005.3.1

  A practical and environmentally friendly organocatalytic strategy designed to mimic the DHAP aldolases has been developed and shown to be effective in the preparation of carbohydrates and aminosugars. (S)-Proline and (S)-2-pyrrolidine-tetrazole catalyzed the aldol reaction between dihydroxy acetone variants such as 1,3-dioxan-5-one and 2,2-dimethyl-1,3-dioxan-5-one with aldehydes to give the corresponding polyols in good yields with very high ees.
• Dihydroxyacetone Variants in the Organocatalytic Construction of Carbohydrates:  Mimicking Tagatose and Fuculose Aldolases
  作者：Jeff T. Suri、Susumu Mitsumori、Klaus Albertshofer、Fujie Tanaka、Carlos F. Barbas

  DOI：10.1021/jo0602017

  日期：2006.5.1

  Dihydroxyacetone variants have been explored as donors in organocatalytic aldol reactions with various aldehyde and ketone acceptors. The protected form of dihydroxyacetone that was chosen for in-depth study was 2,2-dimethyl-1,3-dioxan-5-one, 1. Among the catalysts surveyed here, proline proved to be superior in terms of yield and stereoselectivities in the construction of various carbohydrate scaffolds. In a fashion analogous to aldolase enzymes, the de novo preparation of L-ribulose, L-lyxose, D-ribose, D-tagatose, 1-amino-1-deoxy-D-lyxitol, and other carbohydrates was accomplished via the use of 1 and proline. In reactions using 2,2-dimethyl-1,3-dioxan-5-one 1 as a donor, (S)-proline can be used as a functional mimic of tagatose aldolase, whereas (R)-proline can be regarded as an organocatalytic mimic of fuculose aldolase.