allyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside | 1092840-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
• CAS: 1092840-26-0
• 化学式: C₂₅H₃₇NO₁₅
• 分子量: 591.566
• InChiKey: PHXMXXMJNQXLOV-YOJZCWELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.76
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  211.68
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside 在 氧气 、 sodium methylate 、 臭氧 作用下， 以 甲醇 、 水 为溶剂， 反应 21.25h， 生成 2-oxyoethyl β-D-galactopyranosyl-(1→3)-2-deoxy-2-N-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  The development of new molecular tools containing a chemically synthesized carbohydrate ligand for the elucidation of carbohydrate roles via photoaffinity labeling: Carbohydrate–protein interactions are affected by the structures of the glycosidic bonds and the reducing-end sugar

  摘要：

  Photoaffinity labeling technology is a highly efficient method for cloning carbohydrate-binding proteins. When the carbohydrate probes are synthesized according to conventional methods, however, the reducing terminus of the sugar is opened to provide an acyclic structure. Our continued efforts to solve this problem led to the development of new molecular tools with an oligosaccharide structure that contains a phenyldiazirine group for the elucidation of carbohydrate-protein interactions. We investigated whether carbohydrate-lectin interactions are affected by differences in the glycosidic formation and synthesized three types of molecular tools containing Galp-GlcpNAc disaccharide ligands and a photoreactive group (1, 2, 3). Photoaffinity labeling validated the recognition of the new ligand by different glycosidic bonds. Photoaffinity labeling also demonstrated that both the reducing end sugar and non-reducing end sugar recognized the Erythrina cristagalli agglutinin.

  DOI：

  10.1016/j.bmc.2014.06.049
• 作为产物：
  描述：

  allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 溶剂黄146 、 乙二胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 正丁醇 为溶剂， 反应 39.5h， 生成 allyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  The development of new molecular tools containing a chemically synthesized carbohydrate ligand for the elucidation of carbohydrate roles via photoaffinity labeling: Carbohydrate–protein interactions are affected by the structures of the glycosidic bonds and the reducing-end sugar

  摘要：

  Photoaffinity labeling technology is a highly efficient method for cloning carbohydrate-binding proteins. When the carbohydrate probes are synthesized according to conventional methods, however, the reducing terminus of the sugar is opened to provide an acyclic structure. Our continued efforts to solve this problem led to the development of new molecular tools with an oligosaccharide structure that contains a phenyldiazirine group for the elucidation of carbohydrate-protein interactions. We investigated whether carbohydrate-lectin interactions are affected by differences in the glycosidic formation and synthesized three types of molecular tools containing Galp-GlcpNAc disaccharide ligands and a photoreactive group (1, 2, 3). Photoaffinity labeling validated the recognition of the new ligand by different glycosidic bonds. Photoaffinity labeling also demonstrated that both the reducing end sugar and non-reducing end sugar recognized the Erythrina cristagalli agglutinin.

  DOI：

  10.1016/j.bmc.2014.06.049

文献信息

• Application and limitations of the methyl imidate protection strategy of N-acetylglucosamine for glycosylations at O-4: synthesis of Lewis A and Lewis X trisaccharide analogues
  作者：Jenifer L. Hendel、Anderson Cheng、France-Isabelle Auzanneau

  DOI：10.1016/j.carres.2008.08.025

  日期：2008.11

  We describe here the synthesis of the allyl Le(a) trisaccharide antigen as well as that of an analogue of the Le(x) trisaccharide antigen, in which the galactose residue has been replaced by a glucose unit. Although successful fucosylations at O-4 of N-acetylglucosamine acceptors have been reported using perbenzylated thioethyl fucosyl donors under MeOTf activation, such conditions led in our case

  我们在这里描述了烯丙基Le（a）三糖抗原以及Le（x）三糖抗原类似物的合成，其中半乳糖残基已被葡萄糖单元取代。尽管已经报道过在MeOTf活化下使用过苄基硫代乙基岩藻糖基供体在N-4-乙酰氨基葡糖受体的O-4处成功进行岩藻糖基化，但在我们的情况下，这种条件导致我们的受体转化为相应的烷基酰亚胺。确实，在Le（a）类似物的合成中，我们证明了N-乙酰基作为亚氨酸甲酯的暂时保护对于在O-4处岩藻糖基化是有利的。相比之下，我们在此报告，使用过乙酰化的吡喃葡萄糖的α-三氯乙酰亚氨酸作为供体，在N-4乙酰氨基葡萄糖单糖受体的O-4处进行的糖基化在活化的情况下比过量的BF（3）x OEt（2）产生的产率更高。亚胺酯。因此，我们得出结论，在暂时保护N-乙酰基为亚氨酸甲酯的情况下，最好通过MeOTf激活氨基葡萄糖上的硫糖苷供体在糖胺受体的O-4处糖基化，特别是当供体具有高反应性并易于降解时。相反，如果供体和受体可以承受BF（3）x