methyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranosyl-(1-2)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-mannopyranoside | 1057668-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranosyl-(1-2)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-mannopyranoside
• CAS: 1057668-96-8
• 化学式: C₂₆H₃₉NO₁₆
• 分子量: 621.593
• InChiKey: GGFYYECVVRERIK-SJYIMCFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  193.28
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside 、 methyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranosyl-(1-2)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 dimethyl(methylthio)sulfonium triflate 作用下， 以 二氯甲烷 为溶剂， 反应 20.33h， 以77%的产率得到methyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranosyl-(1-2)-[2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-β-D-glucopyranosyl-(1-6)]-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Investigations of Glycosylation Reactions with 2-N-Acetyl-2N,3O-oxazolidinone-Protected Glucosamine Donors

  摘要：

  NIS/AgOTf-promoted glycosylations with ethyl 2,3-N,O-carbonyl-2-deoxy-1-thio-beta-D-glueopyranoside donors can be performed with either alpha- or beta-selectivity by tuning the reaction conditions. Small amounts of AgOTf (0.1 equiv) and short reaction times give beta-selectivity, whereas 0.4 equiv of AgOTf and prolonged reaction times afford alpha-linked products. NMR-monitored glycosylation and anomerization experiments show initial formation of exclusively the beta-linkage, which anomerizes, through an intramolecular mechanism involving an endocyclic C - O bond cleavage, to the alpha-linkage.

  DOI：

  10.1021/jo800971s
• 作为产物：
  描述：

  methyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranosyl-(1-2)-6-O-chloroacetyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-mannopyranoside 在 2,6-二甲基吡啶 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以84%的产率得到methyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranosyl-(1-2)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Investigations of Glycosylation Reactions with 2-N-Acetyl-2N,3O-oxazolidinone-Protected Glucosamine Donors

  摘要：

  NIS/AgOTf-promoted glycosylations with ethyl 2,3-N,O-carbonyl-2-deoxy-1-thio-beta-D-glueopyranoside donors can be performed with either alpha- or beta-selectivity by tuning the reaction conditions. Small amounts of AgOTf (0.1 equiv) and short reaction times give beta-selectivity, whereas 0.4 equiv of AgOTf and prolonged reaction times afford alpha-linked products. NMR-monitored glycosylation and anomerization experiments show initial formation of exclusively the beta-linkage, which anomerizes, through an intramolecular mechanism involving an endocyclic C - O bond cleavage, to the alpha-linkage.

  DOI：

  10.1021/jo800971s