(2R,3S,4S)-1,3,4-tris(benzyloxy)-5-(phenylselenyl)pentan-2-yl formate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4S)-1,3,4-tris(benzyloxy)-5-(phenylselenyl)pentan-2-yl formate
• 英文别名: [(2R,3S,4S)-1,3,4-tris(phenylmethoxy)-5-phenylselanylpentan-2-yl] formate
• 化学式: C₃₃H₃₄O₅Se
• 分子量: 589.59
• InChiKey: CHMLPLKMKQSGME-SLGZMBILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 、 苯硒酚 在 2,4,6-三叔丁基吡啶 、 三氟甲磺酸酐 、 二苯基亚砜 、 甲醇 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以58%的产率得到phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of β-Phenylselenoglycosides from Glycals and Rationalization of the Selenoglycosylation Processes

  摘要：

  beta-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe(-)) with glycals. A rationalization of the presently described beta-selectivity and the opposite alpha-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.

  DOI：

  10.1021/jo100145s

文献信息

• Stereoselective Synthesis of β-Phenylselenoglycosides from Glycals and Rationalization of the Selenoglycosylation Processes
  作者：Valeria Di Bussolo、Annalisa Fiasella、Federica Balzano、Gloria Uccello Barretta、Paolo Crotti

  DOI：10.1021/jo100145s

  日期：2010.6.18

  beta-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe(-)) with glycals. A rationalization of the presently described beta-selectivity and the opposite alpha-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.