(2S,4S,6R)-6-[(2R)-2-[(4-methoxyphenyl)methoxy]butyl]-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-3,3-dimethyl-4-[(2R,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxane | 1450842-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,6R)-6-[(2R)-2-[(4-methoxyphenyl)methoxy]butyl]-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-3,3-dimethyl-4-[(2R,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxane
• CAS: 1450842-84-8
• 化学式: C₃₇H₅₆O₁₀
• 分子量: 660.846
• InChiKey: IAOZIIJDHCJNIF-BLDQOZQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  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 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 121.33h， 生成 (2S,4S,6R)-6-[(2R)-2-[(4-methoxyphenyl)methoxy]butyl]-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-3,3-dimethyl-4-[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxane 、 (2S,4S,6R)-6-[(2R)-2-[(4-methoxyphenyl)methoxy]butyl]-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-3,3-dimethyl-4-[(2R,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxane
  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.