allyl 3-O-(4-methoxybenzyl)-α-D-galactopyranoside | 183954-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-(4-methoxybenzyl)-α-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]-6-prop-2-enoxyoxane-3,5-diol
• CAS: 183954-75-8
• 化学式: C₁₇H₂₄O₇
• 分子量: 340.373
• InChiKey: ZRJLSOLTCSHHCA-ALYAQQCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 3-O-(4-methoxybenzyl)-α-D-galactopyranoside 在 水 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 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：

  4-甲氧基氯苄 、 烯丙基-Α-D-吡喃半乳糖苷 在 二正丁基氧化锡 、 四丁基溴化铵 作用下， 以 苯 为溶剂， 反应 30.0h， 以79%的产率得到allyl 3-O-(4-methoxybenzyl)-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

• Synthesis of Sulfated Galactocerebrosides from an Orthogonal β-D-Galactosylceramide Scaffold for the Study of CD1–Antigen Interactions
  作者：Federica Compostella、Silvia Ronchi、Luigi Panza、Sabrina Mariotti、Lucia Mori、Gennaro De Libero、Fiamma Ronchetti

  DOI：10.1002/chem.200501586

  日期：2006.7.17

  activates T cells. To assess the role of the position of the sulfate in T cell activation, the synthesis of three beta-D-galactosylceramides, variously bearing a sulfate at position 2, 4, or 6 of galactose, has been planned and carried out. The compounds were synthesized by an orthogonal sulfation strategy from a common beta-D-galactosylceramide scaffold, which was in turn obtained through an efficient glycosylation

  CD1a蛋白与硫化物（3-O-磺基-β-D-半乳糖基神经酰胺）结合形成抗原复合物，该复合物与T细胞受体相互作用并激活T细胞。为了评估硫酸盐的位置在T细胞活化中的作用，已经计划并进行了三种在半乳糖的2、4或6位带有硫酸盐的β-D-半乳糖基神经酰胺的合成。这些化合物是通过正交硫酸化策略从常见的β-D-半乳糖基神经酰胺支架合成的，该支架依次通过完全正交保护的半乳糖亚氨酸半乳糖苷和3-O-苯甲酰基叠氮鞘氨醇之间的有效糖基化反应获得。与天然硫化物相比，三种硫酸化化合物在CD1a介导的T细胞活化中的免疫学评估，
• 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.
• Hiruma, Kazumi; Hashimoto, Hironobu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 6, p. 879 - 884
  作者：Hiruma, Kazumi、Hashimoto, Hironobu

  DOI：——

  日期：——
• 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.