3-trifluoroacetamidopropyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside | 497173-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-trifluoroacetamidopropyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 3- trifluoroacetamidopropyl 2-acetamido-3,6-di-O-acetyl-4-O-(2,4,6-tri-O-acetyl-3-O-[2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl]-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-3-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-[3-[(2,2,2-trifluoroacetyl)amino]propoxy]oxan-2-yl]methyl acetate
• CAS: 497173-22-5
• 化学式: C₄₃H₅₉F₃N₂O₂₆
• 分子量: 1076.93
• InChiKey: RJOKULLRXRAKTB-ZZSWAALPSA-N

反应信息

• 作为反应物：
  描述：

  3-trifluoroacetamidopropyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of histo blood-group antigens A and B (type 2), xenoantigen Galα1-3Galβ1-4GlcNAc and related type 2 backbone oligosaccharides as haptens in spacered form

  摘要：

  The partial alpha-fucosylation of spacered (sp = CH2CH2CH2NH2) N-acetyl beta-lactosamine derivative having free hydroxy groups at C-3 and C-2' gives rise to oligosaccharides H (type 2), Le(x) and Le(y), the first one was further elongated giving rise to A (type 2) or B (type 2) tetrasaccharides; spacered trisaccharides Galalpha1-3Galbeta1-4GlcNAc and Galalpha1-4Galbeta1-4GlcNAc were synthesised by the partial alpha-galactosylation of N-acetyl beta-lactosamine derivative, having free hydroxy groups at C-4' and C-3'.

  DOI：

  10.1070/mc2002v012n04abeh001591
• 作为产物：
  描述：

  乙酸酐 、 在 吡啶 作用下， 生成 3-trifluoroacetamidopropyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of histo blood-group antigens A and B (type 2), xenoantigen Galα1-3Galβ1-4GlcNAc and related type 2 backbone oligosaccharides as haptens in spacered form

  摘要：

  The partial alpha-fucosylation of spacered (sp = CH2CH2CH2NH2) N-acetyl beta-lactosamine derivative having free hydroxy groups at C-3 and C-2' gives rise to oligosaccharides H (type 2), Le(x) and Le(y), the first one was further elongated giving rise to A (type 2) or B (type 2) tetrasaccharides; spacered trisaccharides Galalpha1-3Galbeta1-4GlcNAc and Galalpha1-4Galbeta1-4GlcNAc were synthesised by the partial alpha-galactosylation of N-acetyl beta-lactosamine derivative, having free hydroxy groups at C-4' and C-3'.

  DOI：

  10.1070/mc2002v012n04abeh001591

文献信息

• Synthesis of blood group A and B (type 2) tetrasaccharides. A strategy with fucosylation at the last stage
  作者：Roman A. Kunetskiy、Galina V. Pazynina、Igor A. Ivanov、Nicolai V. Bovin

  DOI：10.1016/j.carres.2020.108192

  日期：2020.12

  The traditionally used strategy for the synthesis of blood group A and B tetrasaccharides includes 2'-O-fucosylation of lactosamine followed by insertion of an α1-3 linked N-acetylgalactosamine or a galactose moiety. Here, we report the synthesis of 3-aminopropyl glycosides of A (type 2) and B (type 2) tetrasaccharides via an alternative sequence, i.e. α-galactosaminylation (or α-galactosylation) followed

  传统上用于合成血型 A 和 B 四糖的策略包括乳糖胺的 2'-O-岩藻糖基化，然后插入 α1-3 连接的 N-乙酰半乳糖胺或半乳糖部分。在这里，我们报告了通过替代序列合成 A（2 型）和 B（2 型）四糖的 3-氨基丙基糖苷，即 α-半乳糖胺化（或 α-半乳糖基化），然后是 α-岩藻糖基化。该策略使我们能够合成不含岩藻糖的三糖 GalNAcα1-3Galβ1-4GlcNAc 和 Galα1-3Galβ1-4GlcNAc，它们是利用针对三糖的人类天然抗体进行免疫治疗的有前景的靶标。该方案的关键阶段是在具有第二个 (3-OH) 未保护基团的中间体三糖中对 βGal 的 2'-OH 基团进行选择性氯乙酰化。