allyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside | 402578-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
• 英文别名: pivaloyl(-3)[pivaloyl(-6)]GlcNAc(b1-3)[Bn(-2)][Bn(-4)][Bn(-6)]Gal(a)-O-allyl；[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4S,5R,6S)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-4-yl]oxy-4-(2,2-dimethylpropanoyloxy)-3-hydroxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 402578-76-1
• 化学式: C₄₈H₆₃NO₁₃
• 分子量: 862.027
• InChiKey: ITEITIJXLLROFK-FTRNCVNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  62
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  167
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 在 吡啶 、 三氟甲磺酸 、 水 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.33h， 生成 allyl 3-O-<2-acetamido-2-deoxy-3-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-galactopyranosyl>-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 2,4,6-tri-O-benzyl-α-D-galactopyranoside 在 吡啶 、 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 5.33h， 生成 allyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranosyl-(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

文献信息

• Improvement of the Synthesis of Immunological Carbohydrate Vaccines Containing the Tumour Associate Antigen CaMBr1
  作者：Luigi Lay、Luigi Panza、Laura Poletti、Davide Prosperi、Silvana Canevari、Maria Elisa Perico

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

  日期：2001.11

  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.