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-acetyl-α-D-mannopyranoside | 228699-88-5

• 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->3)-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranoside
• 英文别名: methyl 2,4-di-O-acetyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside；Man2Ac3Ac4Ac6Ac(a1-3)[Man2Ac3Ac4Ac6Ac(a1-6)]a-Man1Me2Ac4Ac；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5S,6S)-3,5-diacetyloxy-6-methoxy-4-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 228699-88-5
• 化学式: C₃₉H₅₄O₂₆
• 分子量: 938.842
• InChiKey: QPLLZDHZDNAOMS-DRDVAMHQSA-N

物化性质

• 沸点：
  826.9±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  65
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  318
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  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-acetyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以93%的产率得到methyl 3,6-di-O-(α-D-mannopyranosyl)-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：

  溶剂黄146 、 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 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以90%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-acetyl-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

文献信息

• A combined intramolecular–intermolecular one-pot glycosylation approach for the synthesis of a branched trisaccharide
  作者：Serafín Valverde、Mercedes García、Ana M. Gómez、J. Cristóbal López

  DOI：10.1039/b000771o

  日期：——

  Intramolecular and intermolecular glycosidic couplings have been combined in a one-pot protocol for the synthesis of a branched trimannan.

  在一个反应体系中结合了分子内和分子间的糖苷连接，以合成一种支链三甘露糖。
• Backinowsky; Abronina; Nepogodiev, Polish Journal of Chemistry, 1999, vol. 73, # 6, p. 955 - 965
  作者：Backinowsky、Abronina、Nepogodiev、Grachev、Kochetkov

  DOI：——

  日期：——