benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1→4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside | 1219003-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1→4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside
• 英文别名: benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1->4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside
• CAS: 1219003-23-2
• 化学式: C₆₃H₆₅NO₂₄
• 分子量: 1220.2
• InChiKey: MVZFWFABSJLJPE-PTNGBAFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  88.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  315.11
• 氢给体数：
  2.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1→4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以97%的产率得到benzyl β-D-galactopyranosyl-(1->2)-β-D-galactofuranosyl-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins

  摘要：

  The trisaccharides beta-D-Galf-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc (5) and beta-D-Galp-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc (6) constitute novel structures isolated as alditols when released by reductive p-elimination from mucins of Trypanosoma cruzi (Tulahuen strain). Trisaccharides 5 and 6 were synthesized employing the aldonolactone approach. Thus, a convenient D-galactono-1,4-lactone derivative was used for the introduction of the internal galactofuranose and the trichloroacetimidate method was employed for glycosylation reactions. Due to the lack of anchimeric assistance on O-2 of the galactofuranosyl precursor, glycosylation studies were performed under different conditions. The nature of the solvent strongly determined the stereochemical course of the glycosylation reactions when the galactofuranosyl donor was substituted either by 2-O-Galp or 2-O-Galf. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.005
• 作为产物：
  描述：

  benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1->4)-2-acetamido-3-O-benzoyl-6-O-t-butyldiphenylsilyl-2-deoxy-α-D-glucopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1→4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins

  摘要：

  The trisaccharides beta-D-Galf-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc (5) and beta-D-Galp-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc (6) constitute novel structures isolated as alditols when released by reductive p-elimination from mucins of Trypanosoma cruzi (Tulahuen strain). Trisaccharides 5 and 6 were synthesized employing the aldonolactone approach. Thus, a convenient D-galactono-1,4-lactone derivative was used for the introduction of the internal galactofuranose and the trichloroacetimidate method was employed for glycosylation reactions. Due to the lack of anchimeric assistance on O-2 of the galactofuranosyl precursor, glycosylation studies were performed under different conditions. The nature of the solvent strongly determined the stereochemical course of the glycosylation reactions when the galactofuranosyl donor was substituted either by 2-O-Galp or 2-O-Galf. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.005

文献信息

• Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides
  作者：Rosalía Agustí、M. Eugenia Giorgi、Verónica M. Mendoza、Gustavo A. Kashiwagi、Rosa M. de Lederkremer、Carola Gallo-Rodriguez

  DOI：10.1016/j.bmc.2015.01.056

  日期：2015.3

  hexasaccharide β-d-Galp-(1→2)-[β-d-Galp-(1→3)]-β-d-Galp-(1→6)-[β-d-Galp(1→2)-β-d-Galf(1→4)]-d-GlcNAc (10) and its β-d-Galf-(1→2)-β-d-Galf containing isomer (7) are the largest carbohydrates in mucins of some strains of Trypanosoma cruzi. The terminal β-d-Galp units are sites of sialylation by the parasite trans-sialidase. Hexasaccharide 10 was chemically synthesized for the first time by a [3+3] nitrilium based

  六糖β- d -Gal p-（1→2）-[β- d- Gal p-（1→3）]-β- d- Gal p-（1→6）-[β- d- Gal p（1→2）-β- d- Gal f（1→4）]- d -GlcNAc（10）及其β- d- Gal f-（1→2）-β- d- Gal f含有异构体（7）是克鲁斯锥虫某些菌株粘蛋白中最大的碳水化合物。末端β- d -Gal p单位是被寄生虫唾液酸化的位点反唾液酸酶。六糖10首次通过基于[3 + 3]腈基的收敛方法化学合成，使用糖基化的三氯乙酰亚氨酸酯方法合成。它的糖醇的1 H NMR谱图与从寄生虫粘蛋白中通过β消除释放的产物的谱图相同。对10的苄基糖苷进行的反唾液酸化反应研究表明，两种单唾液酸化产物的相对丰度随时间变化。另一方面，通过唾液酸化7的苄基糖苷，仅产生一种产物。。后者的制备合成和产物的光谱分析明确地在较少受阻（1→3）连接的吡喃半乳糖上建立了唾液酸化位点。