allyl 4-O-acetyl-2,3-O-isopropylidene-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside | 316382-33-9

• 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: allyl 4-O-acetyl-2,3-O-isopropylidene-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside
• CAS: 316382-33-9
• 化学式: C₂₈H₄₀O₁₆
• 分子量: 632.616
• InChiKey: HXRWEHKPYYMUAT-JYNSOJRUSA-N

物化性质

• 沸点：
  648.1±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.47
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  186.88
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  allyl 4-O-acetyl-2,3-O-isopropylidene-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 在 吡啶 、 tetrafluoroboric acid 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 0.33h， 生成 allyl 2-O-(α-L-arabinofuranosyl)-6-O-(α-D-mannopyranosyl)-β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of allyl 2-O-(α-l-arabinofuranosyl)-6-O-(α-d-mannopyranosyl)-β-d-mannopyranoside, a unique plant N-glycan motif containing arabinose

  摘要：

  The synthesis of the trisaccharide allyl 2-O-(alpha -L-arabinofuranosyl)-6-O-(alpha -D-mannopyranosyl)-beta -D-mannopyranoside is reported. Stereoselective glycosylation at C-6 of a non-protected allyl beta -mannoside with the acetylated alpha -D-mannosyl bromide gave the alpha-(1 --> 6)-disaccharide as the main product and the crystalline 3,6-branched trisaccharide as minor compound. Further glycosylation of the 2,3 diol (1 --> 6) disaccharide with L-arabinofuranosyl bromide furnished a mixture of 3-O- and 2-O-alpha -L-Ara-trisaccharides from which the title compound was isolated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00185-3
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 吡啶 、 camphor-10-sulfonic acid 、 sodium methylate 、 氰化汞 、 溶剂黄146 、 mercury dibromide 、 silver(l) oxide 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 152.0h， 生成 allyl 4-O-acetyl-2,3-O-isopropylidene-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of allyl 2-O-(α-l-arabinofuranosyl)-6-O-(α-d-mannopyranosyl)-β-d-mannopyranoside, a unique plant N-glycan motif containing arabinose

  摘要：

  The synthesis of the trisaccharide allyl 2-O-(alpha -L-arabinofuranosyl)-6-O-(alpha -D-mannopyranosyl)-beta -D-mannopyranoside is reported. Stereoselective glycosylation at C-6 of a non-protected allyl beta -mannoside with the acetylated alpha -D-mannosyl bromide gave the alpha-(1 --> 6)-disaccharide as the main product and the crystalline 3,6-branched trisaccharide as minor compound. Further glycosylation of the 2,3 diol (1 --> 6) disaccharide with L-arabinofuranosyl bromide furnished a mixture of 3-O- and 2-O-alpha -L-Ara-trisaccharides from which the title compound was isolated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00185-3