methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-ethynyl-α-D-mannopyranoside | 466646-26-4

• 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-tri-O-benzyl-6-deoxy-6-C-ethynyl-α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-prop-2-ynyloxane
• CAS: 466646-26-4
• 化学式: C₃₀H₃₂O₅
• 分子量: 472.581
• InChiKey: RENHBDPMKZIWKU-ZNOUKXQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-ethynyl-α-D-mannopyranoside 在 喹啉 、 Lindlar's catalyst 、 palladium on calcium fluoride poisoned with lead 、 氢气 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.08h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-formyl-α-D-mannopyranoside
  参考文献：
  名称：

  Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man and the Disaccharides α-d-Man-(1→3)-d-Man and α-d-Man-(1→6)-d-Man

  摘要：

  Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.

  DOI：

  10.1021/jo020339z
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(trifluoromethanesulfonyl)-α-D-mannopyranoside 在 六甲基磷酰三胺 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-ethynyl-α-D-mannopyranoside
  参考文献：
  名称：

  镍催化还原氢糖基化合成 C-低聚糖

  摘要：

  C-寡糖是含有O / N / S-糖苷键的天然聚糖的代谢稳定替代物，因此具有治疗潜力。在这里，我们报告了一种通过镍催化炔基糖苷与糖基溴的还原氢糖基化合成乙烯基C-连接寡糖的直接方法。

  DOI：

  10.1021/acs.orglett.4c00289