(2S)-2-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-2-(methoxymethoxy)ethanol | 844473-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-2-(methoxymethoxy)ethanol
• 英文别名: (2S)-2-[(4R,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6-phenyl-1,3-dioxan-4-yl]-2-(methoxymethoxy)ethanol
• CAS: 844473-73-0
• 化学式: C₂₂H₃₈O₆Si
• 分子量: 426.626
• InChiKey: VPVOCMITPCEDRH-MTQWCTHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-2-(methoxymethoxy)ethanol 在 2,6-二甲基吡啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxymethoxy)pent-4-enyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane
  参考文献：
  名称：

  Stereoselective Synthesis of the Naturally Occurring Styryllactones (+)-Goniofufurone and (+)-Cardiobutanolide

  摘要：

  The naturally occurring gamma-lactones (+)-goniofufurone 1 and (+)-cardiobutanolide 2, two pharmacologically active products from Goniothalamus species (Annonaceae), have been synthesized in enantiopure form using L-erythrulose as the chiral starting material. Key steps of these syntheses were a stereoselective anti boron aldol reaction and an asymmetric allylboration.

  DOI：

  10.1021/jo0483116
• 作为产物：
  描述：

  (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-(tert-butyldimethylsilyloxy)-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane 在 吡啶 、 potassium carbonate 、 氟化氢吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2S)-2-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-2-(methoxymethoxy)ethanol
  参考文献：
  名称：

  Stereoselective Synthesis of the Naturally Occurring Styryllactones (+)-Goniofufurone and (+)-Cardiobutanolide

  摘要：

  The naturally occurring gamma-lactones (+)-goniofufurone 1 and (+)-cardiobutanolide 2, two pharmacologically active products from Goniothalamus species (Annonaceae), have been synthesized in enantiopure form using L-erythrulose as the chiral starting material. Key steps of these syntheses were a stereoselective anti boron aldol reaction and an asymmetric allylboration.

  DOI：

  10.1021/jo0483116

文献信息

• Stereoselective Synthesis of the Naturally Occurring Styryllactones (+)-Goniofufurone and (+)-Cardiobutanolide
  作者：Purificación Ruiz、Juan Murga、Miguel Carda、J. Alberto Marco

  DOI：10.1021/jo0483116

  日期：2005.1.1

  The naturally occurring gamma-lactones (+)-goniofufurone 1 and (+)-cardiobutanolide 2, two pharmacologically active products from Goniothalamus species (Annonaceae), have been synthesized in enantiopure form using L-erythrulose as the chiral starting material. Key steps of these syntheses were a stereoselective anti boron aldol reaction and an asymmetric allylboration.