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 | 1046456-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: methyl (4S,4aR,6S,8S,8aR)-8-acetyloxy-4-[(1R)-1,2-diacetyloxyethyl]-2-oxo-6-phenylsulfanyl-1,4,4a,7,8,8a-hexahydropyrano[3,2-d][1,3]oxazine-6-carboxylate
• CAS: 1046456-68-1
• 化学式: C₂₃H₂₇NO₁₁S
• 分子量: 525.533
• InChiKey: ZSNIMPUAEDRCCS-GAQSFIOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  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 、 methyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside 在 silver perchlorate 、 一溴化碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 methyl 2,4,6-tri-O-benzyl-3-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 2,4,6-tri-O-benzyl-3-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
• 作为产物：
  描述：

  methyl (phenyl 5-amino-5-N,7-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)uronate 、 乙酸酐 在 吡啶 作用下， 反应 3.5h， 以94%的产率得到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
  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