(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 | 851040-42-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (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
• CAS: 851040-42-1
• 化学式: C₃₄H₆₄O₆Si₂
• 分子量: 625.05
• InChiKey: AYHUQQCSCQUTCA-ZJRZZCDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.64
• 重原子数：
  42
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (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 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以86%的产率得到(4R,15R,16R,21S)-rollicosin
  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 、 a,6-lutidine 、 AD-mix-β 、 氢气 、 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 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 、 叔丁醇 、 苯 为溶剂， -78.0~110.0 ℃ 、101.33 kPa 条件下， 反应 69.58h， 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

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.