N-acetyl-4,7,8,9-tetra-O-benzyloxymethyl-2-deoxy-neuraminic acid methyl ester | 1001847-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-4,7,8,9-tetra-O-benzyloxymethyl-2-deoxy-neuraminic acid methyl ester
• CAS: 1001847-19-3
• 化学式: C₄₄H₅₃NO₁₂
• 分子量: 787.904
• InChiKey: KTSJLQOAXDHOAW-JXJYPIDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  57.0
• 可旋转键数：
  25.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  138.47
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-benzyloxymethyl-2-deoxy-neuraminic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.5h， 以100%的产率得到N-acetyl-4,7,8,9-tetra-O-benzyloxymethyl-2-deoxy-neuraminic acid
  参考文献：
  名称：

  Stereocontrolled and Convergent Entry to CF₂-Sialosides:  Synthesis of CF₂-Linked Ganglioside GM4

  摘要：

  Sialidase-resistant ganglioside analogues having biological activities similar to those of natural gangliosides are expected to be important probes for clarifying the biological functions of gangliosides. Focusing on difluoromethylene-linked (CF2-linked) alpha(2,3) sialylgalactose as a core structure of sialidase-resistant ganglioside mimics, we have developed novel, stereocontrolled, and efficient methodologies to synthesize CF2-sialosides based on Ireland-Claisen rearrangement. CF2-linked alpha(2,3)sialylgalactose and CF2-linked GM4 were synthesized.

  DOI：

  10.1021/ja075738w
• 作为产物：
  描述：

  苄基氯甲基醚 、 Methyl 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以85%的产率得到N-acetyl-4,7,8,9-tetra-O-benzyloxymethyl-2-deoxy-neuraminic acid methyl ester
  参考文献：
  名称：

  Stereocontrolled and Convergent Entry to CF₂-Sialosides:  Synthesis of CF₂-Linked Ganglioside GM4

  摘要：

  Sialidase-resistant ganglioside analogues having biological activities similar to those of natural gangliosides are expected to be important probes for clarifying the biological functions of gangliosides. Focusing on difluoromethylene-linked (CF2-linked) alpha(2,3) sialylgalactose as a core structure of sialidase-resistant ganglioside mimics, we have developed novel, stereocontrolled, and efficient methodologies to synthesize CF2-sialosides based on Ireland-Claisen rearrangement. CF2-linked alpha(2,3)sialylgalactose and CF2-linked GM4 were synthesized.

  DOI：

  10.1021/ja075738w