(5R,10S)-10-allyl-5-((2R,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-dodecyltetrahydro-2Hpyran-2-yl)-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-6-yne | 1073515-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,10S)-10-allyl-5-((2R,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-dodecyltetrahydro-2Hpyran-2-yl)-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-6-yne
• 英文别名: [(2R,3R,6R)-6-[(1R,6S)-1,6-bis[[tert-butyl(dimethyl)silyl]oxy]non-8-en-2-ynyl]-2-dodecyloxan-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1073515-96-4
• 化学式: C₄₄H₈₈O₄Si₃
• 分子量: 765.437
• InChiKey: BQBXKXRIVJAKJZ-JYSLIDIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.38
• 重原子数：
  51
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,10S)-10-allyl-5-((2R,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-dodecyltetrahydro-2Hpyran-2-yl)-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-6-yne 、 9-硼双环[3.3.1]壬烷 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  A Concise and Modular Synthesis of Pyranicin

  摘要：

  A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.

  DOI：

  10.1021/ol802041c
• 作为产物：
  描述：

  (1R,6S)-6-((tert-butyldimethylsilyl)oxy)-1-((2R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-dodecyltetrahydro-2H-pyran-2-yl)non-8-en-2-yn-1-ol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到(5R,10S)-10-allyl-5-((2R,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-dodecyltetrahydro-2Hpyran-2-yl)-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-6-yne
  参考文献：
  名称：

  A Concise and Modular Synthesis of Pyranicin

  摘要：

  A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.

  DOI：

  10.1021/ol802041c

文献信息

• A Concise and Modular Synthesis of Pyranicin
  作者：Nolan D. Griggs、Andrew J. Phillips

  DOI：10.1021/ol802041c

  日期：2008.11.6

  A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.