(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 | 1133062-97-1

• 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,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
• CAS: 1133062-97-1
• 化学式: C₃₇H₄₆O₆
• 分子量: 586.769
• InChiKey: NKRCDFPXQZWAOC-LIEAFEJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  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

文献信息

• β-Glycosidation of Sterically Hindered Alcohols
  作者：Alex M. Szpilman、Erick M. Carreira

  DOI：10.1021/ol9000735

  日期：2009.3.19

  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.