(2S,3R,4R,5R,6R)-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-phenylselanyl-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-ol | 1228930-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R,6R)-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-phenylselanyl-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-ol
• CAS: 1228930-06-0
• 化学式: C₆₀H₆₂O₁₀Se
• 分子量: 1022.11
• InChiKey: AXLKFEJQOKAUNZ-IJAHBILKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.99
• 重原子数：
  71
• 可旋转键数：
  24
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  苯硒酚 、 hexa-O-benzyl lactal 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78%的产率得到(2S,3R,4R,5R,6R)-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-phenylselanyl-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-ol
  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.