[(3R,3'aR,6'R,6'aR)-7-iodo-2',2',4-trimethylspiro[1H-2-benzofuran-3,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]-6'-yl]methoxy-tert-butyl-dimethylsilane | 909107-82-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [(3R,3'aR,6'R,6'aR)-7-iodo-2',2',4-trimethylspiro[1H-2-benzofuran-3,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]-6'-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 909107-82-0
• 化学式: C₂₂H₃₃IO₅Si
• 分子量: 532.491
• InChiKey: OLOCKVFDDRISBX-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3R,3'aR,6'R,6'aR)-7-iodo-2',2',4-trimethylspiro[1H-2-benzofuran-3,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]-6'-yl]methoxy-tert-butyl-dimethylsilane 、 4-甲氧基苯硼酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex potassium phosphate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以89%的产率得到[(3R,3'aR,6'R,6'aR)-7-(4-methoxyphenyl)-2',2',4-trimethylspiro[1H-2-benzofuran-3,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]-6'-yl]methoxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Synthesis of Spirocyclic C-Arylribosides via Cyclotrimerization

  摘要：

  Spirocyclic C-arylribosides were synthesized from the known-ribonolactone derivative. Lithium acetylide addition followed by glycosylation with 3-(trimethylsilyl) propargyl alcohol converted the ribonolactone to silylated diynes. After desilylation or iodination, subsequent rutheniumcatalyzed cycloaddition of resultant diynes with alkynes or chloroacetonitrile gave spirocyclic C-arylribosides.

  DOI：

  10.1021/ol061350e
• 作为产物：
  描述：

  3-[[(3aR,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4-prop-1-ynyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]oxy]prop-1-ynyl-trimethylsilane 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) N-碘代丁二酰亚胺 、 silver nitrate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 [(3R,3'aR,6'R,6'aR)-7-iodo-2',2',4-trimethylspiro[1H-2-benzofuran-3,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]-6'-yl]methoxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Synthesis of Spirocyclic C-Arylribosides via Cyclotrimerization

  摘要：

  Spirocyclic C-arylribosides were synthesized from the known-ribonolactone derivative. Lithium acetylide addition followed by glycosylation with 3-(trimethylsilyl) propargyl alcohol converted the ribonolactone to silylated diynes. After desilylation or iodination, subsequent rutheniumcatalyzed cycloaddition of resultant diynes with alkynes or chloroacetonitrile gave spirocyclic C-arylribosides.

  DOI：

  10.1021/ol061350e