(1R,2R,4S,4'S,5'R)-4'-((tert-butyldimethylsilyl)oxy)-5'-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-7-methyl-4',5'-dihydro-2'H-5-oxaspiro[bicyclo[2.2.2]octane-2,3'-furan]-7-ene-2',6-dione | 1449574-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2R,4S,4'S,5'R)-4'-((tert-butyldimethylsilyl)oxy)-5'-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-7-methyl-4',5'-dihydro-2'H-5-oxaspiro[bicyclo[2.2.2]octane-2,3'-furan]-7-ene-2',6-dione
• CAS: 1449574-97-3
• 化学式: C₂₄H₄₂O₇Si₂
• 分子量: 498.764
• InChiKey: TZRNVSWDTQMTLD-KCWNILAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,4'S,5'R)-4'-((tert-butyldimethylsilyl)oxy)-5'-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-7-methyl-4',5'-dihydro-2'H-5-oxaspiro[bicyclo[2.2.2]octane-2,3'-furan]-7-ene-2',6-dione 在 三乙胺 作用下， 以 氯苯 为溶剂， 反应 0.5h， 以68%的产率得到(3R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-3-(((tert-butyldimethylsilyl)oxy)methyl)-7-methyl-2-oxaspiro[4.5]dec-7-ene-1,6-dione
  参考文献：
  名称：

  Concise Synthesis of the Multiply Oxygenated ABC-Ring System of the Dihydro-β-agarofurans

  摘要：

  The multiply oxygenated ABC-ring system of the dihydro-beta-agarofurans was synthesized by employing two highly stereoselective reactions. The quinidine-catalyzed Diels-Alder reaction between a chiral dienophile and 3-hydroxy-4-methyl-2-pyrone simultaneously installed the C2-stereogenic center and two contiguous tetrasubstituted carbon centers (C5 and C10) of the A-ring. After 12 additional transformations, the aldol reaction of the resulting spiral AC-ring cyclized the B-ring with stereoselective introduction of the C7- and C8-centers.

  DOI：

  10.1021/ol402038b
• 作为产物：
  描述：

  3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylene-hydroxy-2-propenoic acid methyl ester 在 2,6-二甲基吡啶 、 盐酸 、 奎尼丁 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (1R,2R,4S,4'S,5'R)-4'-((tert-butyldimethylsilyl)oxy)-5'-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-7-methyl-4',5'-dihydro-2'H-5-oxaspiro[bicyclo[2.2.2]octane-2,3'-furan]-7-ene-2',6-dione
  参考文献：
  名称：

  Concise Synthesis of the Multiply Oxygenated ABC-Ring System of the Dihydro-β-agarofurans

  摘要：

  The multiply oxygenated ABC-ring system of the dihydro-beta-agarofurans was synthesized by employing two highly stereoselective reactions. The quinidine-catalyzed Diels-Alder reaction between a chiral dienophile and 3-hydroxy-4-methyl-2-pyrone simultaneously installed the C2-stereogenic center and two contiguous tetrasubstituted carbon centers (C5 and C10) of the A-ring. After 12 additional transformations, the aldol reaction of the resulting spiral AC-ring cyclized the B-ring with stereoselective introduction of the C7- and C8-centers.

  DOI：

  10.1021/ol402038b