p-methoxyphenyl 4,6-O-benzylidene-2-O-tris(isopropyl)silyl-β-D-galactopyranoside | 1001847-16-0

• 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-2-O-tris(isopropyl)silyl-β-D-galactopyranoside
• CAS: 1001847-16-0
• 化学式: C₂₉H₄₂O₇Si
• 分子量: 530.734
• InChiKey: QPXGHXATXXGEDM-TYXMGCQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 4,6-O-benzylidene-2-O-tris(isopropyl)silyl-β-D-galactopyranoside 在 乙酸酐 、 二甲基亚砜 作用下， 反应 10.5h， 以93%的产率得到p-methoxyphenyl 4,6-O-benzylidene-2-O-tris(isopropyl)silyl-β-D-xylo-hex-3-ulopyranoside
  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-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