(2S,6R)-6-[(2R)-2-hydroxybutyl]-2-(2-hydroxyethyl)-3,3-dimethyloxan-4-one | 1450842-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S,6R)-6-[(2R)-2-hydroxybutyl]-2-(2-hydroxyethyl)-3,3-dimethyloxan-4-one
• CAS: 1450842-77-9
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: STRGIFODBBLUBE-FOGDFJRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6R)-6-[(2R)-2-hydroxybutyl]-2-(2-hydroxyethyl)-3,3-dimethyloxan-4-one 在 sodium tetrahydroborate 、 2,6-二叔丁基-4-甲基苯酚 、 4-甲基苯磺酸吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 124.33h， 生成 (R)-1-((2R,4S,6S)-6-(2-hydroxyethyl)-5,5-dimethyl-4-(((2S,3R,4S,5R)-3,4,5-trimethoxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)butan-2-ol
  参考文献：
  名称：

  Formation of Highly Substituted Tetrahydropyranones: Application to the Total Synthesis of Cyanolide A

  摘要：

  A new tetrahydropyranone synthesis has been developed that leads to cis-2,6-disubstituted 3,3-dimethyltetrahydropyran-4-one rings by condensation of an aldehyde and a hydroxy silyl enol ether. The reaction works with a variety of aldehydes to produce the tetrahydropyranone products in moderate to high yields. This new method was applied to the enantioselective synthesis of cyanolide A and its aglycone.

  DOI：

  10.1021/ol402095g
• 作为产物：
  描述：

  3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enoic acid ethyl ester 在 二乙基甲氧基硼烷 、 三氟化硼乙醚 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 33.5h， 生成 (2S,6R)-6-[(2R)-2-hydroxybutyl]-2-(2-hydroxyethyl)-3,3-dimethyloxan-4-one
  参考文献：
  名称：

  Formation of Highly Substituted Tetrahydropyranones: Application to the Total Synthesis of Cyanolide A

  摘要：

  A new tetrahydropyranone synthesis has been developed that leads to cis-2,6-disubstituted 3,3-dimethyltetrahydropyran-4-one rings by condensation of an aldehyde and a hydroxy silyl enol ether. The reaction works with a variety of aldehydes to produce the tetrahydropyranone products in moderate to high yields. This new method was applied to the enantioselective synthesis of cyanolide A and its aglycone.

  DOI：

  10.1021/ol402095g

文献信息

• Formation of Highly Substituted Tetrahydropyranones: Application to the Total Synthesis of Cyanolide A
  作者：Gidget C. Tay、Michael R. Gesinski、Scott D. Rychnovsky

  DOI：10.1021/ol402095g

  日期：2013.9.6

  A new tetrahydropyranone synthesis has been developed that leads to cis-2,6-disubstituted 3,3-dimethyltetrahydropyran-4-one rings by condensation of an aldehyde and a hydroxy silyl enol ether. The reaction works with a variety of aldehydes to produce the tetrahydropyranone products in moderate to high yields. This new method was applied to the enantioselective synthesis of cyanolide A and its aglycone.