p-methoxyphenyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-2-O-tris(isopropyl)silyl-β-D-galactopyranoside | 1001847-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-2-O-tris(isopropyl)silyl-β-D-galactopyranoside
• CAS: 1001847-15-9
• 化学式: C₃₇H₅₀O₈Si
• 分子量: 650.885
• InChiKey: YHWVJOSCTJRFSE-NFFSMVTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.07
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-2-O-tris(isopropyl)silyl-β-D-galactopyranoside 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到p-methoxyphenyl 4,6-O-benzylidene-2-O-tris(isopropyl)silyl-β-D-galactopyranoside
  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：

  p-methoxyphenyl 4,6-O-benzylidene-3-O-tris(isopropyl)silyl-β-D-galactopyranoside 、 4-甲氧基溴苄 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以91%的产率得到p-methoxyphenyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-2-O-tris(isopropyl)silyl-β-D-galactopyranoside
  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