allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside | 316382-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside
• CAS: 316382-37-3
• 化学式: C₅₃H₅₈O₂₄
• 分子量: 1079.03
• InChiKey: PXYDFTPHBOLFBS-UQXAICGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  77.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  292.08
• 氢给体数：
  0.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以12 mg的产率得到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 、 tetrafluoroboric acid 、 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 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 152.33h， 生成 allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-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