(1R)-3-(ethyl 2-methyl-2-propanoate)-9,9-di-tert-butyl-2,8,10-trioxa-9-silabicyclo[5.4.0]-5,6-dibromoundecane | 1190738-90-9

• 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: (1R)-3-(ethyl 2-methyl-2-propanoate)-9,9-di-tert-butyl-2,8,10-trioxa-9-silabicyclo[5.4.0]-5,6-dibromoundecane
• 英文别名: ethyl 2-[(4aR,6S,8S,9S,9aS)-8,9-dibromo-2,2-ditert-butyl-4a,6,7,8,9,9a-hexahydro-4H-[1,3,2]dioxasilino[5,4-b]oxepin-6-yl]-2-methylpropanoate
• CAS: 1190738-90-9
• 化学式: C₂₁H₃₈Br₂O₅Si
• 分子量: 558.423
• InChiKey: FOGFSKDRNAZQHO-NNXHMXCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-3-(ethyl 2-methyl-2-propanoate)-9,9-di-tert-butyl-2,8,10-trioxa-9-silabicyclo[5.4.0]-5,6-dibromoundecane 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 2.0h， 以58%的产率得到ethyl 2-[(2S,4S,5S,6S,7R)-4,5-dibromo-6-hydroxy-7-(hydroxymethyl)oxepan-2-yl]-2-methylpropanoate
  参考文献：
  名称：

  Heptanosides from Galactose-Derived Oxepenes via Stereoselective Addition Reactions

  摘要：

  Addition reactions to a 3,4-anhydroheptanose gave heptanoside analogues of carbohydrate derivatives in good to excellent stereochemical purity. Characterization of the products by H-1 and C-13 NMR, COSY, HSQC-DEPT, HMBC, 1D TOCSY, and NOE experiments were performed to obtain the stereochemistry of addition. The 3,4-anhydroheptanose used in this study is obtained from the ring-expansion of a cyclopropanated galactal and thus demonstrates the synthetic utility of heptanose synthesis via cyclopropanated carbohydrates.

  DOI：

  10.1021/jo901706e
• 作为产物：
  描述：

  ethyl 2-[(4aR,6S,9aR)-2,2-ditert-butyl-4a,6,7,9a-tetrahydro-4H-[1,3,2]dioxasilino[5,4-b]oxepin-6-yl]-2-methylpropanoate 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以84.9 mg的产率得到(1R)-3-(ethyl 2-methyl-2-propanoate)-9,9-di-tert-butyl-2,8,10-trioxa-9-silabicyclo[5.4.0]-5,6-dibromoundecane
  参考文献：
  名称：

  Heptanosides from Galactose-Derived Oxepenes via Stereoselective Addition Reactions

  摘要：

  Addition reactions to a 3,4-anhydroheptanose gave heptanoside analogues of carbohydrate derivatives in good to excellent stereochemical purity. Characterization of the products by H-1 and C-13 NMR, COSY, HSQC-DEPT, HMBC, 1D TOCSY, and NOE experiments were performed to obtain the stereochemistry of addition. The 3,4-anhydroheptanose used in this study is obtained from the ring-expansion of a cyclopropanated galactal and thus demonstrates the synthetic utility of heptanose synthesis via cyclopropanated carbohydrates.

  DOI：

  10.1021/jo901706e