methyl (2R,4S,5R,6R)-5-[[2-[(2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-2-yl]oxyacetyl]amino]-4-hydroxy-2-prop-2-enoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | 474452-49-8

• 英文名称: methyl (2R,4S,5R,6R)-5-[[2-[(2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-2-yl]oxyacetyl]amino]-4-hydroxy-2-prop-2-enoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 474452-49-8
• 化学式: C₃₅H₅₂N₂O₂₂
• 分子量: 852.798
• InChiKey: CMRADBNWSLYHPW-NEYDWBQBSA-N

物化性质

• 沸点：
  979.7±65.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  59
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  334
• 氢给体数：
  6
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl (2R,4S,5R,6R)-5-[[2-[(2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-2-yl]oxyacetyl]amino]-4-hydroxy-2-prop-2-enoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate 在 吡啶 作用下， 反应 16.0h， 以80%的产率得到methyl (2R,4S,5R,6R)-5-[[2-[(2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-2-yl]oxyacetyl]amino]-4-acetyloxy-2-prop-2-enoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Neu5Acα(2→5)Neu5Gc:  The Building Block of Oligo/Poly(→5-O_glycolylNeu5Gcα2→) Chains in Sea Urchin Egg Cell Surface Glycoprotein

  摘要：

  The synthesis of a sialic acid dimer derivative, Neu5Acalpha(2-->5)Neu5Gc, is described. The synthetic strategy is based on the use of allyl alcohol to achieve an exclusive alpha-sialylation product. The allyloxy group is also a latent glycolic acid that provides the subsequent coupling with neuraminate with minimal protection-deprotection manipulations.

  DOI：

  10.1021/jo025988p
• 作为产物：
  描述：

  allyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,54-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid methyl ester 在 三甲基氯硅烷 、 四甲基氢氧化铵 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 46.0h， 生成 methyl (2R,4S,5R,6R)-5-[[2-[(2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-2-yl]oxyacetyl]amino]-4-hydroxy-2-prop-2-enoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Neu5Acα(2→5)Neu5Gc:  The Building Block of Oligo/Poly(→5-O_glycolylNeu5Gcα2→) Chains in Sea Urchin Egg Cell Surface Glycoprotein

  摘要：

  The synthesis of a sialic acid dimer derivative, Neu5Acalpha(2-->5)Neu5Gc, is described. The synthetic strategy is based on the use of allyl alcohol to achieve an exclusive alpha-sialylation product. The allyloxy group is also a latent glycolic acid that provides the subsequent coupling with neuraminate with minimal protection-deprotection manipulations.

  DOI：

  10.1021/jo025988p