[(3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 2-chloro-2-methylpropanoate | 1133063-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 2-chloro-2-methylpropanoate
• CAS: 1133063-10-1
• 化学式: C₃₃H₃₅Cl₄NO₇
• 分子量: 699.455
• InChiKey: VJODMQFEEDIWCF-XSXASNHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 2-chloro-2-methylpropanoate 、 胆固醇 在 2-chloro-6-methylpyridinium triflate 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以67%的产率得到
  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.