Methyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-di-O-benzylidene-α-D-mannopyranoside | 245366-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-di-O-benzylidene-α-D-mannopyranoside
• 英文别名: methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside；[(2R,3S,4S,5R,6R)-2-[[(2R,4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 245366-63-6
• 化学式: C₅₀H₅₄O₁₂
• 分子量: 846.972
• InChiKey: JDSRLPMJYGAABC-QFDJWNTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  62
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Methyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-di-O-benzylidene-α-D-mannopyranoside 在 硼烷四氢呋喃络合物 、 copper(II) bis(trifluoromethanesulfonate) 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Sonication-Assisted Oligomannoside Synthesis

  摘要：

  We have investigated the use of sonication for the synthesis of oligomannosides. A convenient sonication-mediated glycosylation protocol that is applicable to traditional glycosylation methods has been developed. This protocol can be applicable for activating glycosyl donors that are known to have low reactivity which enable the synthesis of oligomannosides of particular biological interest with the same efficiency.

  DOI：

  10.1021/jo8019835
• 作为产物：
  描述：

  ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 、 methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到Methyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-di-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and Conformational Analysis of a Conformationally Constrained Trisaccharide, and Complexation Properties with Concanavalin A

  摘要：

  The trisaccharide beta-D-GlcNAc(1 --> 2)alpha-D-Man(1 --> 3)D-Man is a fragment of a biantennary glycan that is recognized by alpha-D-Man-specific lectins such as concanavalin A (ConA), Lathyrus ochrus lectin, lentil lectin, and can adopt several conformations upon binding. To probe the importance of loss of flexibility of a saccharide during binding with ConA this trisaccharide has been synthesized in a conformationally constrained form where a methylene acetal bridge mimics a GlcNAc-O-6 "...Man-O-4 intramolecular hydrogen bond. Microcalorimetry measurements revealed that the conformationally constrained compound has a more favorable entropy term but this term is offset by a smaller enthalpy term. NMR spectroscopic studies have shown that the cyclic compound is indeed considerably less flexible than the linear compound and both compounds adopt mainly one conformation. SYBYL software together with energy parameters appropriate for carbohydrates was used for a systematic conformational search. The linear compound is very flexible. A clustering method determined seven main conformational families. Six possible conformational families were identified for the cyclic compound when considering the orientations of the beta GlcNAc(1 --> 2)Man and alpha beta Man-(1 --> 3)Man glycosidic bonds. The central mannose residue was docked in the binding site of ConA and the complex was refined. The results are compared with crystal structures of legume lectin oligosaccharide complexes and with the NMR and thermodynamic data.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2281::aid-chem2281>3.0.co;2-d