(3R,5R)-7-[tert-butyl(dimethyl)silyl]oxy-8-methylnon-7-ene-3,5-diol | 1450842-64-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,5R)-7-[tert-butyl(dimethyl)silyl]oxy-8-methylnon-7-ene-3,5-diol
• CAS: 1450842-64-4
• 化学式: C₁₆H₃₄O₃Si
• 分子量: 302.53
• InChiKey: LAOCHHISAQPCMZ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5R)-7-[tert-butyl(dimethyl)silyl]oxy-8-methylnon-7-ene-3,5-diol 在 sodium tetrahydroborate 、 2,6-二叔丁基-4-甲基苯酚 、 三氟化硼乙醚 、 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 128.33h， 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：

  1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 在 二乙基甲氧基硼烷 、 异丙基氯化镁 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 环己烷 为溶剂， 反应 44.5h， 生成 (3R,5R)-7-[tert-butyl(dimethyl)silyl]oxy-8-methylnon-7-ene-3,5-diol
  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

• Silyl Enol Ether Prins Cyclization: Diastereoselective Formation of Substituted Tetrahydropyran-4-ones
  作者：Gidget C. Tay、Chloe Y. Huang、Scott D. Rychnovsky

  DOI：10.1021/jo501580p

  日期：2014.9.19

  developed. The key step of this methodology, a silyl enol ether Prins cyclization, was promoted by a condensation reaction between a hydroxy silyl enol ether and an aldehyde to afford substituted tetrahydropyran-4-ones. The cyclization was tolerant of many functional groups, and the modular synthesis of the hydroxy silyl enol ether allowed for the formation of more than 30 new tetrahydropyran-4-ones with

  开发了顺式-2,6-二取代四氢吡喃-4-酮的非对映选择性合成方法。该方法的关键步骤是羟基甲硅烷基烯醇醚和醛之间的缩合反应，以得到取代的四氢吡喃-4-酮，从而促进甲硅烷基烯醇醚Prins环化。环化能够耐受许多官能团，并且羟基硅基烯醇醚的模块化合成允许形成超过 30 种新的四氢吡喃-4-酮，产率高达 97% 和 >95:5 dr。环化步骤形成新的碳-碳和碳-氧键，以及具有良好非对映选择性的四元中心。该方法为取代四氢吡喃的合成提供了一条通用途径。
• 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.