(5R)-5-[(1R,12R)-1-[tert-butyl(dimethyl)silyl]oxy-12,13-dihydroxytridecyl]oxolan-2-one | 851040-40-9

• 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)-5-[(1R,12R)-1-[tert-butyl(dimethyl)silyl]oxy-12,13-dihydroxytridecyl]oxolan-2-one
• CAS: 851040-40-9
• 化学式: C₂₃H₄₆O₅Si
• 分子量: 430.701
• InChiKey: MEBQQRNLXHPXSU-NJDAHSKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R)-5-[(1R,12R)-1-[tert-butyl(dimethyl)silyl]oxy-12,13-dihydroxytridecyl]oxolan-2-one 在 a,6-lutidine 、 双(三甲基硅烷基)氨基钾 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.5h， 生成 (2S)-4-[(2R,13R)-2,13-bis[[tert-butyl(dimethyl)silyl]oxy]-13-[(2R)-5-oxooxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-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：

  11-(benzyloxy)-1-undecene 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 、 palladium on activated charcoal 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 AD-mix-β 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 叔丁醇 、 苯 为溶剂， -10.0~80.0 ℃ 、101.33 kPa 条件下， 反应 52.08h， 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

文献信息

• Asymmetric Total Synthesis of Rollicosin
  作者：Kevin J. Quinn、André K. Isaacs、Brian A. DeChristopher、Stephanie C. Szklarz、Rebecca A. Arvary

  DOI：10.1021/ol047352l

  日期：2005.3.1

  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.