allyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside | 402578-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
• CAS: 402578-89-6
• 化学式: C₇₂H₇₉NO₁₆
• 分子量: 1214.42
• InChiKey: ZKIRUVDNYFDGGA-UFPCVUHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.89
• 重原子数：
  89.0
• 可旋转键数：
  29.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  178.55
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-tri-O-benzyl-α/β-L-fucopyranosyl) trichloroacetimidate 、 allyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到allyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Improvement of the Synthesis of Immunological Carbohydrate Vaccines Containing the Tumour Associate Antigen CaMBr1

  摘要：

  The simplified synthesis of a portion of Globo-H hexasaccharide, a saccharide antigen overexpressed by breast cancer cells, and its conjugation to two different immunogenic proteins are described, The conjugated vaccines, evaluated in a preclinical model, showed good immunogenic potential.

  DOI：

  10.1002/1099-0690(200111)2001:22<4331::aid-ejoc4331>3.0.co;2-r
• 作为产物：
  描述：

  allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 14.0h， 生成 allyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Improvement of the Synthesis of Immunological Carbohydrate Vaccines Containing the Tumour Associate Antigen CaMBr1

  摘要：

  The simplified synthesis of a portion of Globo-H hexasaccharide, a saccharide antigen overexpressed by breast cancer cells, and its conjugation to two different immunogenic proteins are described, The conjugated vaccines, evaluated in a preclinical model, showed good immunogenic potential.

  DOI：

  10.1002/1099-0690(200111)2001:22<4331::aid-ejoc4331>3.0.co;2-r