benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1->4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside | 1219003-09-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(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: N-[(2S,3R,4R,5S,6R)-4-benzoyloxy-5-[(2R,3R,4S,5S)-4-benzoyloxy-3-[(2S,3R,4S,5S)-3,4-dibenzoyloxy-5-[(1R)-1,2-dibenzoyloxyethyl]oxolan-2-yl]oxy-5-[(1R)-1,2-dibenzoyloxyethyl]oxolan-2-yl]oxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]ethanimidic acid
• CAS: 1219003-09-4
• 化学式: C₈₃H₇₃NO₂₄
• 分子量: 1468.48
• InChiKey: CZTKRFZFAIDSNP-UUBUZBQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  108
• 可旋转键数：
  37
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  319
• 氢给体数：
  2
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(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， 反应 3.0h， 以95%的产率得到benzyl β-D-galactofuranosyl-(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 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1->4)-2-acetamido-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranoside 在 氢氟酸 、 水 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以88%的产率得到benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(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：

  所述的合成ø -连接的含有六糖β- d -Gal ˚F - （1→2）-β- d -Gal ˚F在克氏锥虫粘蛋白†

  摘要：

  六糖β- D -Gal p-（1→2）-[β- D -Gal p-（1→3）]-β- D -Gal p-（1→6）-[β- D -Gal f（1→2）-β- d -Gal ˚F（1→4）] - d -GlcNAc（1）是从一些菌株的粘蛋白释放作为醛糖醇通过还原性β-消除最大碳水化合物结构锥虫。末端β- D- Gal p单位是通过反唾液酸酶进行唾液酸化的位点，其将唾液酸从宿主转移至寄生虫。六糖1通过基于腈辅助糖基化的[3 + 3]聚合策略，使用三氯乙酰亚氨酸酯方法合成了SnO。所述β- d -Gal ˚F - （1→2）-β- d -Gal ˚F - d -GlcNAc合成子依次从还原端构造成的非还原端使用苄α- d -galactofuranoside作为起始原料内部Gal f单元。对这种新型前体的选择是在一个反应​​步骤中从半乳糖中获得的，从而可以在O-2处引入一个正交的参与的乙酰丙酰基。因此，Gal

  DOI：

  10.1039/c2ob25741f

文献信息

• Synthesis of the O-linked hexasaccharide containing β-d-Galf-(1→2)-β-d-Galf in Trypanosoma cruzi mucins
  作者：Gustavo A. Kashiwagi、Verónica M. Mendoza、Rosa M. de Lederkremer、Carola Gallo-Rodriguez

  DOI：10.1039/c2ob25741f

  日期：——

  hexasaccharide β-D-Galp-(1→2)-[β-D-Galp-(1→3)]-β-D-Galp-(1→6)-[β-D-Galf(1→2)-β-D-Galf(1→4)]-D-GlcNAc (1) is the largest carbohydrate structure released as alditol by reductive β-elimination from mucins of some strains of T. cruzi. The terminal β-D-Galp units are sites of sialylation by trans-sialidase which transfers sialic acid from the host to the parasite. Hexasaccharide 1 was synthesized by a [3 + 3]-convergent

  六糖β- D -Gal p-（1→2）-[β- D -Gal p-（1→3）]-β- D -Gal p-（1→6）-[β- D -Gal f（1→2）-β- d -Gal ˚F（1→4）] - d -GlcNAc（1）是从一些菌株的粘蛋白释放作为醛糖醇通过还原性β-消除最大碳水化合物结构锥虫。末端β- D- Gal p单位是通过反唾液酸酶进行唾液酸化的位点，其将唾液酸从宿主转移至寄生虫。六糖1通过基于腈辅助糖基化的[3 + 3]聚合策略，使用三氯乙酰亚氨酸酯方法合成了SnO。所述β- d -Gal ˚F - （1→2）-β- d -Gal ˚F - d -GlcNAc合成子依次从还原端构造成的非还原端使用苄α- d -galactofuranoside作为起始原料内部Gal f单元。对这种新型前体的选择是在一个反应​​步骤中从半乳糖中获得的，从而可以在O-2处引入一个正交的参与的乙酰丙酰基。因此，Gal
• Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins
  作者：Verónica M. Mendoza、Gustavo A. Kashiwagi、Rosa M. de Lederkremer、Carola Gallo-Rodriguez

  DOI：10.1016/j.carres.2009.12.005

  日期：2010.2

  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.