phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside | 149202-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aR)-2-phenyl-7,8-bis(phenylmethoxy)-6-phenylselanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 149202-89-1
• 化学式: C₃₃H₃₂O₅Se
• 分子量: 587.574
• InChiKey: HQMKPOWFMJBNAX-REQNJXLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 以92%的产率得到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
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside 在 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-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

文献信息

• Novel glycosidation methodology. The use of phenyl selenoglycosides as glycosyl donors and acceptors in oligosaccharide synthesis
  作者：Seema Mehta、B. Mario Pinto

  DOI：10.1021/jo00064a012

  日期：1993.6

  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.