allyl 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-α-D-galactopyranoside | 183954-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-α-D-galactopyranoside
• 英文别名: Bn(-2)[Mob(-3)][Bn(-4)][Bn(-6)]Gal(a)-O-allyl；(2R,3S,4S,5R,6S)-4-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxane
• CAS: 183954-76-9
• 化学式: C₃₈H₄₂O₇
• 分子量: 610.747
• InChiKey: DPQVKRVFNPLGLH-LDVAZLSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-α-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 4.0h， 以71%的产率得到allyl 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：

  烯丙基-Α-D-吡喃半乳糖苷 在 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 反应 7.0h， 生成 allyl 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin

  摘要：

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.

  DOI：

  10.1021/ja9611093

文献信息

• Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin
  作者：Kazumi Hiruma、Tetsuya Kajimoto、Gabriel Weitz-Schmidt、Ian Ollmann、Chi-Huey Wong

  DOI：10.1021/ja9611093

  日期：1996.1.1

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.
• 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.