(R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-dodecyl]-dihydro-furan-2-one | 851040-39-6

• 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: (R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-dodecyl]-dihydro-furan-2-one
• CAS: 851040-39-6
• 化学式: C₂₂H₄₄O₄Si
• 分子量: 400.674
• InChiKey: UREPSSVSZRPUJC-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  27.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-dodecyl]-dihydro-furan-2-one 在 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 AD-mix-β 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 36.08h， 生成 (5R)-5-[(1R,12R)-1-[tert-butyl(dimethyl)silyl]oxy-12,13-dihydroxytridecyl]oxolan-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Rollicosin

  摘要：

  The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation.

  DOI：

  10.1021/ol047352l
• 作为产物：
  描述：

  (2R)-2-[(E,1R)-1-[tert-butyl(dimethyl)silyl]oxy-12-phenylmethoxydodec-2-enyl]-2H-furan-5-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以86%的产率得到(R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-dodecyl]-dihydro-furan-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Rollicosin

  摘要：

  The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation.

  DOI：

  10.1021/ol047352l