methyl α-D-glucopyranosyl-(1->3)-α-D-mannopyranosyl-(1->2)-α-D-mannopyranoside | 216758-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-D-glucopyranosyl-(1->3)-α-D-mannopyranosyl-(1->2)-α-D-mannopyranoside
• 英文别名: Glc(a1-3)Man(a1-2)a-Man1Me；(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 216758-92-8
• 化学式: C₁₉H₃₄O₁₆
• 分子量: 518.469
• InChiKey: KATKVTYIFRVOJG-NMCCMINVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl α-D-glucopyranosyl-(1->3)-α-D-mannopyranosyl-(1->2)-α-D-mannopyranoside 以 吡啶 为溶剂， 生成 methyl (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1-3)-(2,4,6-tri-O-acetyl-α-Dmannopyranosyl)-(1-2)-3,4,6-tri-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein

  摘要：

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.

  DOI：

  10.1080/07328309808001894
• 作为产物：
  描述：

  methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 在 10% palladium on active carbon N-碘代丁二酰亚胺 、 叔丁基二甲硅基三氟甲磺酸酯 、 水 、 氢气 、 silver trifluoromethanesulfonate 、 二正丁基氧化锡 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 三乙胺 、 甲苯 为溶剂， -50.0~20.0 ℃ 、101.33 kPa 条件下， 反应 140.15h， 生成 methyl α-D-glucopyranosyl-(1->3)-α-D-mannopyranosyl-(1->2)-α-D-mannopyranoside
  参考文献：
  名称：

  A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein

  摘要：

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.

  DOI：

  10.1080/07328309808001894

文献信息

• Synthesis of the tetrasaccharide α-d-Glcp-(1→3)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp recognized by Calreticulin/Calnexin
  作者：Emiliano Gemma、Martina Lahmann、Stefan Oscarson

  DOI：10.1016/j.carres.2005.09.001

  日期：2005.11

  The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-alpha-D-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete alpha-selectivity, a disaccharide building block in high yield. The

  使用嵌段合成方法有效地合成了标题化合物作为其甲基糖苷。6-O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃葡萄糖基碘化物与乙基2-O-乙酰基-4,6-二-O-苄基-1-硫代烃之间的卤化物辅助糖基化使用三苯基氧化膦作为促进剂的β-α-D-甘露吡喃糖苷以完全的α-选择性产生了高产率的二糖结构单元。事实证明，该化合物的过苄基化衍生物是出色的供体，它以NIS / AgOTf促进的偶联方式提供88％的受保护目标四糖与已知的甲基二甘露糖苷受体。然后通过催化氢解脱保护得到目标化合物，总产率为47％。