(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-hydroxy-6-hydroxymethyl-1-cyclohexanone | 649572-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-hydroxy-6-hydroxymethyl-1-cyclohexanone
• 英文别名: (1R,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-2-one
• CAS: 649572-45-2
• 化学式: C₁₃H₂₄O₅Si
• 分子量: 288.416
• InChiKey: ZPJKECNKQOPCQL-MITHSLQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-hydroxy-6-hydroxymethyl-1-cyclohexanone 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (+)-(5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)methyl acetate
  参考文献：
  名称：

  Total synthesis of (+)-epiepoformin and (−)-phyllostine

  摘要：

  An efficient asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine has been achieved using the chiral building block available from the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Since (-)-theobroxide was derived from the same precursor of (+)-epiepoformin, the formal total synthesis of (-)-theobroxide has also been achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.065
• 作为产物：
  描述：

  (-)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methylene-1-cyclohexanone 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 24.0h， 以99%的产率得到(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-hydroxy-6-hydroxymethyl-1-cyclohexanone
  参考文献：
  名称：

  Total synthesis of (+)-epiepoformin and (−)-phyllostine

  摘要：

  An efficient asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine has been achieved using the chiral building block available from the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Since (-)-theobroxide was derived from the same precursor of (+)-epiepoformin, the formal total synthesis of (-)-theobroxide has also been achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.065