phenyl 2,3,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside | 149180-13-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside
• CAS: 149180-13-2
• 化学式: C₃₃H₃₄O₅Se
• 分子量: 589.59
• InChiKey: MUBYWMLAENEVFX-AALIFHQRSA-N

物化性质

• 沸点：
  696.0±55.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate 、 phenyl 2,3,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 在 三乙基硅基三氟甲磺酸酯 作用下， 生成 phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1-seleno-β-D-glucopyranoside
  参考文献：
  名称：

  Novel glycosidation methodology. The use of phenyl selenoglycosides as glycosyl donors and acceptors in oligosaccharide synthesis

  摘要：

  The use of phenyl selenoglycosides as glycosyl donors and acceptors in glycosidation reactions is described. The versatility of these novel compounds is illustrated by the selective activation of both ''disarmed'' and ''armed'' phenyl selenoglycoside donors over ''armed'' ethyl thioglycoside acceptors with silver trifluoromethanesulfonate in the presence of potassium or silver carbonate to give disaccharides in excellent yield. Selective activation of glycosyl bromide donors over phenyl selenoglycoside acceptors is realized by silver trifluoromethanesulfonate promotion in the presence of collidine. Such selectivity is also demonstrated by the activation of a glycosyl trichloroacetimidate donor in the presence of selenoglycoside acceptors with triethylsilyl trifluoromethanesulfonate. The central role of selenoglycosides is illustrated by the synthesis of a trisaccharide that profits from the sequential, selective activation of a glycosyl bromide donor over a selenoglycoside acceptor and the resulting disaccharide selenoglycoside over a thioglycoside acceptor. The liberation of the anomeric hydroxyl group from a phenyl selenoglycoside is also described.

  DOI：

  10.1021/jo00064a012
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 盐酸 、 三氟化硼乙醚 、 sodium methylate 、 次磷酸 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 phenyl 2,3,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside
  参考文献：
  名称：

  Novel glycosidation methodology. The use of phenyl selenoglycosides as glycosyl donors and acceptors in oligosaccharide synthesis

  摘要：

  The use of phenyl selenoglycosides as glycosyl donors and acceptors in glycosidation reactions is described. The versatility of these novel compounds is illustrated by the selective activation of both ''disarmed'' and ''armed'' phenyl selenoglycoside donors over ''armed'' ethyl thioglycoside acceptors with silver trifluoromethanesulfonate in the presence of potassium or silver carbonate to give disaccharides in excellent yield. Selective activation of glycosyl bromide donors over phenyl selenoglycoside acceptors is realized by silver trifluoromethanesulfonate promotion in the presence of collidine. Such selectivity is also demonstrated by the activation of a glycosyl trichloroacetimidate donor in the presence of selenoglycoside acceptors with triethylsilyl trifluoromethanesulfonate. The central role of selenoglycosides is illustrated by the synthesis of a trisaccharide that profits from the sequential, selective activation of a glycosyl bromide donor over a selenoglycoside acceptor and the resulting disaccharide selenoglycoside over a thioglycoside acceptor. The liberation of the anomeric hydroxyl group from a phenyl selenoglycoside is also described.

  DOI：

  10.1021/jo00064a012