(S)-4-((S)-1-hydroxy-3-methylbutyl)-2,2-dimethyl-1,3-dioxan-5-one | 850426-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-((S)-1-hydroxy-3-methylbutyl)-2,2-dimethyl-1,3-dioxan-5-one
• 英文别名: (1'S,4S)-4-(1'-hydroxy-3'-methyl)butyl-2,2-dimethyl-[1,3]dioxan-5-one；(4S)-4-[(1S)-1-hydroxy-3-methylbutyl]-2,2-dimethyl-1,3-dioxan-5-one
• CAS: 850426-82-3
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: RXTMAYOHJITWLW-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二硝基苯甲酰氯 、 (S)-4-((S)-1-hydroxy-3-methylbutyl)-2,2-dimethyl-1,3-dioxan-5-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3,5-Dinitro-benzoic acid (S)-1-((S)-2,2-dimethyl-5-oxo-[1,3]dioxan-4-yl)-3-methyl-butyl ester
  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
• 作为产物：
  描述：

  异戊醛 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 L-脯氨酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 (S)-4-((S)-1-hydroxy-3-methylbutyl)-2,2-dimethyl-1,3-dioxan-5-one
  参考文献：
  名称：

  A Tandem Organocatalytic α-Chlorination–Aldol Reaction That Proceeds with Dynamic Kinetic Resolution: A Powerful Tool for Carbohydrate Synthesis

  摘要：

  A tandem, proline-catalyzed alpha-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of alpha-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.

  DOI：

  10.1021/ol401370b

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.
• Method for the Production of a-(Alpha-Hydroxyalkyl)-1,3 Dioxan-5-Ones
  申请人：Hayat Nasir

  公开号：US20080097113A1

  公开（公告）日：2008-04-24

  A process for the synthesis of compounds of general formulas comprising the step of reacting in the presence of wherein: R=substituted or unsubstituted alkyl, aryl, heterocycles containing one or more O, N, S, P or B; R 1 and R 2 independently represent H, substituted or unsubstituted alkyl, aryl, heterocycles containing one or more O, N, S, P or B; R′═H, OH, OR or OSiX 3 , wherein X independently represent alkyl or aryl.
• US7851639B2
  申请人：——

  公开号：US7851639B2

  公开（公告）日：2010-12-14