O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1-6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-acetyl-1-N--α-D-glucopyranosylamine | 97347-06-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1-6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-acetyl-1-N--α-D-glucopyranosylamine
• CAS: 97347-06-3
• 化学式: C₆₈H₉₅N₇O₃₆
• 分子量: 1586.53
• InChiKey: JYSRQJVWGINFFV-GBTRVPRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.75
• 重原子数：
  111.0
• 可旋转键数：
  39.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  568.61
• 氢给体数：
  8.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1-6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-acetyl-1-N--α-D-glucopyranosylamine 在 三乙胺 作用下， 以 甲醇 为溶剂， 以74.9%的产率得到O-α-D-glucopyranosyl-(1-6)-O-β-D-glucopyranosyl-(1-6)-1-N--α-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis of N-glycopeptides and a neoglycoprotein

  摘要：

  O-(alpha-D-Glucopyranosyl)-(1----6)-O-beta-D-glucopyranosyl-(1----6)-1-N -(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-alpha- D -glucopyranosylamine has been prepared, as a model of a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding L-glutamyl derivative of the trisaccharide with the pentapeptide in the presence of O,O-diethyl cyanophosphonate. Protective groups were removed by O-deacetylation, deethoxylation, and hydrogenolysis. The glutamyl derivative of the trisaccharide was also converted into the acyl azide which was condensed with bovine serum albumin to form a neoglycoprotein.

  DOI：

  10.1016/0008-6215(85)90014-x
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1[*]6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1[*]6)-2,3,4-tri-O-acetyl-N-(1-ethyl L-glutam-5-oyl)-α-D-glucopyranosylamine 、 N-(benzyloxycarbonyl)glycylglycylglycyl-L-serin-L-leucine 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以55.3%的产率得到O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1-6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-acetyl-1-N--α-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis of N-glycopeptides and a neoglycoprotein

  摘要：

  O-(alpha-D-Glucopyranosyl)-(1----6)-O-beta-D-glucopyranosyl-(1----6)-1-N -(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-alpha- D -glucopyranosylamine has been prepared, as a model of a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding L-glutamyl derivative of the trisaccharide with the pentapeptide in the presence of O,O-diethyl cyanophosphonate. Protective groups were removed by O-deacetylation, deethoxylation, and hydrogenolysis. The glutamyl derivative of the trisaccharide was also converted into the acyl azide which was condensed with bovine serum albumin to form a neoglycoprotein.

  DOI：

  10.1016/0008-6215(85)90014-x