甲基3-O-(2’,3’,4’,6’-O-四乙酰基-alpha-D-甘露糖基)-alpha-D-吡喃甘露糖苷 | 71978-78-4

• 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
• 中文名称: 甲基3-O-(2’,3’,4’,6’-O-四乙酰基-alpha-D-甘露糖基)-alpha-D-吡喃甘露糖苷
• 英文名称: Methyl 3-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 71978-78-4
• 化学式: C₂₁H₃₂O₁₅
• 分子量: 524.476
• InChiKey: IGDYHFLKZHDKLM-GJQNYYSDSA-N

物化性质

• 沸点：
  638.3±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  203
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  甲醇 、 甲基3-O-(2’,3’,4’,6’-O-四乙酰基-alpha-D-甘露糖基)-alpha-D-吡喃甘露糖苷 在 sodium methylate 作用下， 以79%的产率得到甲基 3-O-alpha-D-甘露糖基-alpha-D-吡喃甘露糖苷
  参考文献：
  名称：

  Synthesis and Semisynthesis of Some Structural Elements of Oligo-Mannose Type N-Glycoproteins

  摘要：

  For the construction of N-glycoprotein glycan chains, valuable potential glycosyl donors, O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose octaacetate (19) and O-alpha-D-mannopyranosyl-(1-->2)-O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose undecaacetate (20) were obtained in gram-scale by the acetylation and subsequent partial acetolysis of baker's yeast, without the isolation of mannan. The acetolytic products were investigated by matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Octaacetates of mannobiose (1-->3) (11) and (1-->6) (17) were chemically synthesized.

  DOI：

  10.1080/07328309808002903
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.67h， 生成 甲基3-O-(2’,3’,4’,6’-O-四乙酰基-alpha-D-甘露糖基)-alpha-D-吡喃甘露糖苷
  参考文献：
  名称：

  Synthesis and Semisynthesis of Some Structural Elements of Oligo-Mannose Type N-Glycoproteins

  摘要：

  For the construction of N-glycoprotein glycan chains, valuable potential glycosyl donors, O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose octaacetate (19) and O-alpha-D-mannopyranosyl-(1-->2)-O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose undecaacetate (20) were obtained in gram-scale by the acetylation and subsequent partial acetolysis of baker's yeast, without the isolation of mannan. The acetolytic products were investigated by matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Octaacetates of mannobiose (1-->3) (11) and (1-->6) (17) were chemically synthesized.

  DOI：

  10.1080/07328309808002903

文献信息

• Synthesis and Semisynthesis of Some Structural Elements of Oligo-Mannose Type N-Glycoproteins
  作者：Zoltán Szurmai、Lóránt Jánossy、Zoltán Szilágyi、Károly Vékey

  DOI：10.1080/07328309808002903

  日期：1998.4

  For the construction of N-glycoprotein glycan chains, valuable potential glycosyl donors, O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose octaacetate (19) and O-alpha-D-mannopyranosyl-(1-->2)-O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose undecaacetate (20) were obtained in gram-scale by the acetylation and subsequent partial acetolysis of baker's yeast, without the isolation of mannan. The acetolytic products were investigated by matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Octaacetates of mannobiose (1-->3) (11) and (1-->6) (17) were chemically synthesized.