methyl 2,3-di-O-benzyl-6-O-(methyl 4,8,9-tri-O-acetyl-5-amino-5-N,7-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate)-α-D-galactopyranoside | 1046456-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6-O-(methyl 4,8,9-tri-O-acetyl-5-amino-5-N,7-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate)-α-D-galactopyranoside
• CAS: 1046456-75-0
• 化学式: C₃₈H₄₇NO₁₇
• 分子量: 789.788
• InChiKey: OVADLTNDLKDNON-RRCRZTLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  219.14
• 氢给体数：
  2.0
• 氢受体数：
  17.0

反应信息

• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-α-D-galactopyranoside 、 methyl (phenyl 4,8,9-tri-O-acetyl-5-amino-5-N,7-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)uronate 在 silver perchlorate 、 一溴化碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 methyl 2,3-di-O-benzyl-6-O-(methyl 4,8,9-tri-O-acetyl-5-amino-5-N,7-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate)-α-D-galactopyranoside 、 methyl 2,3-di-O-benzyl-6-O-(methyl 4,8,9-tri-O-acetyl-5-amino-5-N,7-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-α-D-galactopyranoside
  参考文献：
  名称：

  Sialylation reactions with 5-N,7-O-carbonyl-protected sialyl donors: unusual stereoselectivity with nitrile solvent assistance

  摘要：

  A 5-N,7-O-carbonyl-protected sialyl donor was synthesized, and, unexpectedly, this donor showed beta-selectivity (alpha/beta = 1/2.4-1/20) on coupling with sugar acceptors in acetonitrile upon treatment with various promoter systems. For the coupling reaction in dichloromethane, a modified Ellervik's method (IBr and AgClO4 center dot H2O) was highly effective in activating the 5-N,7-O-carbonyl donor, providing moderate alpha-selectivity (alpha/beta = similar to 1.8/1). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.05.005