methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate | 844473-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate
• 英文别名: methyl 2-[(4R,4aR,6R,7S,7aS)-7-(methoxymethoxy)-2,2-dimethyl-4-phenyl-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-6-yl]acetate
• CAS: 844473-76-3
• 化学式: C₁₉H₂₆O₇
• 分子量: 366.411
• InChiKey: MDOACAIMRLAXFT-SOVHRIKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate 在 二甲基硫 、 三氟化硼乙醚 作用下， 反应 0.67h， 以66%的产率得到(+)-goniofufurone
  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：

  (2R)-2-[(4R,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6-phenyl-1,3-dioxan-4-yl]-2-(methoxymethoxy)acetaldehyde 在 4-二甲氨基吡啶 、 氢氧化钾 、 四丁基氟化铵 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate
  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.