ethyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside | 1057668-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(3aR,4S,6R,7S,7aR)-3-acetyl-7-acetyloxy-4-ethylsulfanyl-2-oxo-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-6-yl]methyl acetate
• CAS: 1057668-80-0
• 化学式: C₁₅H₂₁NO₈S
• 分子量: 375.4
• InChiKey: KPYHYZBVKDMBCR-KSTCHIGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  9

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 、 甲基 2,3-O-异亚丙基-alpha-L-吡喃鼠李糖苷 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 0.83h， 以91%的产率得到methyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-β-D-glucopyranosyl-(1-4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  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：

  ethyl 4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside 、 乙酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到ethyl 2-acetamido-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside
  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