(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)oxy)tetrahydro-2H-pyran-3-yl 2-chloro-2-methylpropanoate | 1133062-96-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)oxy)tetrahydro-2H-pyran-3-yl 2-chloro-2-methylpropanoate
• CAS: 1133062-96-0
• 化学式: C₄₁H₅₁ClO₇
• 分子量: 691.305
• InChiKey: DGUYQXFVMPQSLB-NADYZSOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.26
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)oxy)tetrahydro-2H-pyran-3-yl 2-chloro-2-methylpropanoate 在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以88%的产率得到(2R,3R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1R,2S,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]oxy]oxan-3-ol
  参考文献：
  名称：

  β-Glycosidation of Sterically Hindered Alcohols

  摘要：

  The 2-chloro-2-methylpropanoic ester serves as a steering group in the Schmidt glycosidation reaction. Rapid and efficient glycosidation of a range of sterically hindered alcohols takes place under mild, acidic conditions to afford the glycoside products in high yield and beta-selectivity and without formation of orthoester side products. The 2-chloro-2-methylpropanoic ester is readily cleaved under mild, basic conditions.

  DOI：

  10.1021/ol9000735
• 作为产物：
  描述：

  [(3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 2-chloro-2-methylpropanoate 、 (+)-冰片 在 2-chloro-6-methylpyridinium triflate 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以68%的产率得到(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)oxy)tetrahydro-2H-pyran-3-yl 2-chloro-2-methylpropanoate
  参考文献：
  名称：

  β-Glycosidation of Sterically Hindered Alcohols

  摘要：

  The 2-chloro-2-methylpropanoic ester serves as a steering group in the Schmidt glycosidation reaction. Rapid and efficient glycosidation of a range of sterically hindered alcohols takes place under mild, acidic conditions to afford the glycoside products in high yield and beta-selectivity and without formation of orthoester side products. The 2-chloro-2-methylpropanoic ester is readily cleaved under mild, basic conditions.

  DOI：

  10.1021/ol9000735