methyl 6-deoxy-6-C-(1'-(1'-deoxy-α-D-mannopyranosyl)methyl)-α-D-mannopyranoside | 466646-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-C-(1'-(1'-deoxy-α-D-mannopyranosyl)methyl)-α-D-mannopyranoside
• 英文别名: (2R,3S,4R,5S,6R)-2-(hydroxymethyl)-6-[2-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]ethyl]oxane-3,4,5-triol
• CAS: 466646-30-0
• 化学式: C₁₄H₂₆O₁₀
• 分子量: 354.354
• InChiKey: NZZFEUNDIKEEJZ-LPELKEAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 6-deoxy-6-C-(1'-(1'-deoxy-α-D-mannopyranosyl)methyl)-α-D-mannopyranoside 在 吡啶 作用下， 以19 mg的产率得到methyl 2,3,4-tri-O-acetyl-6-deoxy-6-C-(1'-(2',3',4',6'-tetra-O-acetyl-1'deoxy-α-D-mannopyranosyl)methyl)-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：

  甲基-D-丙噻 在 palladium on activated charcoal 咪唑 、 2,6-二甲基吡啶 、 喹啉 、 Lindlar's catalyst 、 samarium diiodide 、 偶氮二异丁腈 、 五氟苯酚 、 palladium on calcium fluoride poisoned with lead 、 三苯基氢化锡 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 臭氧 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 10.25h， 生成 methyl 6-deoxy-6-C-(1'-(1'-deoxy-α-D-mannopyranosyl)methyl)-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

文献信息

• Application of the Anomeric Samarium Route for the Convergent Synthesis of the <i>C</i>-Linked Trisaccharide α-<scp>d</scp>-Man-(1→3)-[α-<scp>d</scp>-Man-(1→6)]-<scp>d</scp>-Man and the Disaccharides α-<scp>d</scp>-Man-(1→3)-<scp>d</scp>-Man and α-<scp>d</scp>-Man-(1→6)-<scp>d</scp>-Man
  作者：Lise Munch Mikkelsen、Sussie Lerche Krintel、Jesús Jiménez-Barbero、Troels Skrydstrup

  DOI：10.1021/jo020339z

  日期：2002.9.1

  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.