(3S,5S,6S)-3-((S)-1-Hydroxy-2-methyl-propyl)-5,6-diphenyl-[1,4]dioxan-2-one | 302842-84-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3S,5S,6S)-3-((S)-1-Hydroxy-2-methyl-propyl)-5,6-diphenyl-[1,4]dioxan-2-one
• 英文别名: (3S,5S,6S)-3-[(1S)-1-hydroxy-2-methylpropyl]-5,6-diphenyl-1,4-dioxan-2-one
• CAS: 302842-84-8
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: KSFXBGGETXICJB-VJANTYMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (3S,5S,6S)-3-((S)-1-Hydroxy-2-methyl-propyl)-5,6-diphenyl-[1,4]dioxan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以73%的产率得到(2S,3S)-2,3-Dihydroxy-4-methyl-pentanoic acid
  参考文献：
  名称：

  Anti-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate

  摘要：

  GRAPHICSThe boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.

  DOI：

  10.1021/ol0002166
• 作为产物：
  描述：

  异丁醛 、 (5S,6S)-5,6-diphenyl-1,4-dioxan-2-one 在 三乙胺 、 双环己基(三氟甲烷磺酰氧基)硼烷 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3R,5S,6S)-3-((R)-1-Hydroxy-2-methyl-propyl)-5,6-diphenyl-[1,4]dioxan-2-one 、 (3S,5S,6S)-3-((S)-1-Hydroxy-2-methyl-propyl)-5,6-diphenyl-[1,4]dioxan-2-one
  参考文献：
  名称：

  Anti-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate

  摘要：

  GRAPHICSThe boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.

  DOI：

  10.1021/ol0002166

文献信息

• <i>Anti</i>-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate
  作者：Merritt B. Andrus、B. B. V. Soma Sekhar、Erik L. Meredith、N. Kent Dalley

  DOI：10.1021/ol0002166

  日期：2000.9.1

  GRAPHICSThe boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.