(2R,3R,4R,5R,6R)-2-(2,6-dimethylphenoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol | 1133063-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6R)-2-(2,6-dimethylphenoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 1133063-03-2
• 化学式: C₃₅H₃₈O₆
• 分子量: 554.683
• InChiKey: URXFUHSNQDPBHJ-JLLSYCQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以47%的产率得到2,6-dimethylphenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside
  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.