(5R,7S,7aR)-5,7-bis(tert-butyldimethylsilyloxy)-7a-[(trimethylsilyl)methyl]-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one | 1250265-32-7

• 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: (5R,7S,7aR)-5,7-bis(tert-butyldimethylsilyloxy)-7a-[(trimethylsilyl)methyl]-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one
• 英文别名: (5R,7S,7aR)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-7a-(trimethylsilylmethyl)-4,5,6,7-tetrahydro-1-benzofuran-2-one
• CAS: 1250265-32-7
• 化学式: C₂₄H₄₈O₄Si₃
• 分子量: 484.899
• InChiKey: XGJCEPYXTZROFR-JXALWOEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,7S,7aR)-5,7-bis(tert-butyldimethylsilyloxy)-7a-[(trimethylsilyl)methyl]-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D₃

  摘要：

  The A-rings of calcitriol (1 alpha,25-dihydeoxyvitamin D-3) and 1 alpha-hydroxy-3-deoxyvitamin D-3 were synthesized using the furan approach The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)-propanal. a diostereoselective Friedel-Crafts hydroxyalkylation an oxidation of the 2.3-disubstituted furan to give a gamma-hydroxybutenolide and a Peterson olefinatiion The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield

  DOI：

  10.1021/jo101155c
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以0.549 g的产率得到(5R,7S,7aR)-5,7-bis(tert-butyldimethylsilyloxy)-7a-[(trimethylsilyl)methyl]-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one
  参考文献：
  名称：

  Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D₃

  摘要：

  The A-rings of calcitriol (1 alpha,25-dihydeoxyvitamin D-3) and 1 alpha-hydroxy-3-deoxyvitamin D-3 were synthesized using the furan approach The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)-propanal. a diostereoselective Friedel-Crafts hydroxyalkylation an oxidation of the 2.3-disubstituted furan to give a gamma-hydroxybutenolide and a Peterson olefinatiion The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield

  DOI：

  10.1021/jo101155c