methyl [p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-benzoyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate | 1356459-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-benzoyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate
• CAS: 1356459-39-6
• 化学式: C₄₇H₄₃NO₁₂S
• 分子量: 845.924
• InChiKey: UZZZZJCMVINRAJ-JQVJFOHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  61.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  169.83
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl [p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-benzoyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate 、 双丙酮半乳糖 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-benzoyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->6)-1,2,3,4-di-O-isopropylidene-α-D-galactopyranoside 、 methyl 5-acetamido-4,7,8,9-tetra-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2->6)-1,2,3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  How O-Substitution of Sialyl Donors Affects Their Stereoselectivity

  摘要：

  The profound effect of substituents at C-5 of glycosyl sialosides on their stereoselectivity is well-known although the exact nature of this effect is somewhat less understood. Presented herein is a comparative study of a range of novel sialyl donors with various O-substituents. It is demonstrated that O-substituents at C-4 and C-7 may also have a significant effect on the reactivity of sialyl donors and on the stereoselectivity of chemical sialylation.

  DOI：

  10.1021/ol3000475
• 作为产物：
  描述：

  苯甲酰氯 、 methyl (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-(p-tolylthio)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以69%的产率得到methyl [p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-benzoyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate
  参考文献：
  名称：

  How O-Substitution of Sialyl Donors Affects Their Stereoselectivity

  摘要：

  The profound effect of substituents at C-5 of glycosyl sialosides on their stereoselectivity is well-known although the exact nature of this effect is somewhat less understood. Presented herein is a comparative study of a range of novel sialyl donors with various O-substituents. It is demonstrated that O-substituents at C-4 and C-7 may also have a significant effect on the reactivity of sialyl donors and on the stereoselectivity of chemical sialylation.

  DOI：

  10.1021/ol3000475