methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-benzyl-α-D-mannopyranoside | 208758-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-benzyl-α-D-mannopyranoside
• 英文别名: Man2Ac3Ac4Ac6Ac(a1-6)[Bn(-2)][Bn(-4)]a-Man1Me；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[[(2R,3S,4S,5S,6S)-4-hydroxy-6-methoxy-3,5-bis(phenylmethoxy)oxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 208758-70-7
• 化学式: C₃₅H₄₄O₁₅
• 分子量: 704.725
• InChiKey: UUSKPEGKBNZXDM-FMBIHKNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  181
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-benzyl-α-D-mannopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 methyl α-D-mannopyranosyl-(1->6)-3-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Anomalous Zemplén deacylation reactions of α- and β-d-mannopyranoside derivatives

  摘要：

  Reaction of mono-, di-, and trisaccharide derivatives of methyl beta -D- and octyl beta -D-mannopyranosides bearing ester groups at isolated and non-isolated positions on the same molecule, under Zemplen conditions (catalytic amount of sodium methoxide in methanol) gave partially deacylated compounds, in which the O-acyl groups were retained at isolated sites. In the case of one disaccharide, all the benzoyl groups remained intact at the reducing end, while all the acetyl functions were removable from the nonreducing end. In another case, both isolated ester groups at positions 2 and 4 were retained at the reducing end. The isolated 2-O-acyl groups on methyl alpha -D-mannopyranoside compounds were more labile than on the corresponding beta -mannosides under the same conditions. The mechanism of the reaction may be different for ester groups at isolated or non-isolated positions. In the latter case, acyl migration may take place and carry acyl groups into a less hindered position. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00283-4
• 作为产物：
  描述：

  甲基2,4-二-O-苄基吡喃己糖苷 、 2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 4 A molecular sieve 、 mercury dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以18.4%的产率得到methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-benzyl-α-D-mannopyranoside
  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