benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside | 502435-29-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside
• 英文别名: benzyl (2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-(1-4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside；Bz(-2)[Bz(-3)][Bz(-5)][Bz(-6)]Galf(b1-4)[Bz(-3)]GlcNAc(a)-O-Bn；[(2R)-2-[(2S,3S,4R,5R)-5-[(2R,3S,4R,5R,6S)-5-acetamido-4-benzoyloxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-3-yl]oxy-3,4-dibenzoyloxyoxolan-2-yl]-2-benzoyloxyethyl] benzoate
• CAS: 502435-29-2
• 化学式: C₅₆H₅₁NO₁₆
• 分子量: 994.018
• InChiKey: ZQBYJKCFFRPECO-PNLFXSNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  73
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  218
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  O-[2,3-di-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-di-O-acetyl-α-D-galactopyranosyl] trichloroacetimidate 、 benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以57%的产率得到
  参考文献：
  名称：

  Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase

  摘要：

  The mucin-like glycoproteins of Trypanosoma cruzi have novel O-linked oligosaccharides that are acceptors of sialic acid in the trans-sialidase (TcTS) reaction. The transference of sialic acid from host glycoconjugates to the mucins is involved in infection and pathogenesis. The synthesis of the pentasaccharide, beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 43)]-beta-D-Galp-(1 -> 6)-[beta-D-Galf-(1 -> 4)]-D-GlcpNAc and the corresponding alditol, previously isolated by reductive beta-elimination of the mucins, is described. The key step was the 6-O-glycosylation of a easily accessible derivative of beta-D-Galf-(1 -> 4)-D-GlcpNAc with a beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 3)]-D-Galp donor using the trichloroacetimidate method. The P-linkage was diastereoselectively obtained by the nitrile effect. The pentasaccharide is the major oligosaccharide in the mucins of T. cruzi, G strain and presents two terminal beta-D-Galp residues for possible sialylation by TcTS. A preparative sialylation reaction was performed with its benzyl glycoside and the sialylated product was isolated and characterized. NMR spectroscopic analysis showed that selective monosialylation occurred at the terminal (1 -> 3) linked galactopyranose. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.033
• 作为产物：
  描述：

  N-苯甲酰咪唑 在 氢氟酸 、 四氯化锡 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 98.0h， 生成 benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->4)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  β-d-Gal的合成p - （1→3）-β-d-Gal的p - （1→6） - [β-d-Gal的˚F - （1→4）] - d-GlcNAc的，四糖组分克氏锥虫的粘蛋白

  摘要：

  游离β-d-Gal的合成p（1→3）-β-d-Gal的- p - （1→6） - [β-d-Gal的˚F - （1→4）] - d-GlcNAc的和描述了先前已经通过还原性β-消除克氏锥虫糖蛋白分离的相应的糖醇。会聚路径通过冷凝β-d-Gal的的受体衍生物设想˚F - （1→4）-D-GlcNAc的具有β-d-Gal的供体衍生物p - （1→3）-D-半乳糖p。三氯乙酰亚胺酸盐方法以及SnCl 4促进的缩合用于引入半乳糖呋喃糖基单元。另一方面，用糖基-醛糖内酯方法，然后用二异戊基硼烷还原内酯，再异构化为半乳糖吡喃糖构型，得到供体衍生物，其通过三氯乙酰亚氨酸酯方法缩合。此外，对于引入β-d-Gal的的合成子p - （1→3）-D-半乳糖˚F单元进行说明。

  DOI：

  10.1016/s0040-4020(02)01226-7

文献信息

• Synthesis of β-d-Galp-(1→3)-β-d-Galp-(1→6)-[β-d-Galf-(1→4)]-d-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
  作者：Carola Gallo-Rodriguez、M.Agustina Gil-Libarona、Verónica M Mendoza、Rosa M de Lederkremer

  DOI：10.1016/s0040-4020(02)01226-7

  日期：2002.11

  The synthesis of free β-d-Galp-(1→3)-β-d-Galp-(1→6)-[β-d-Galf-(1→4)]-d-GlcNAc and the corresponding alditol which has been previously isolated by reductive β-elimination of Trypanosoma cruzi glycoproteins are described. A convergent route was envisioned by condensing an acceptor derivative of β-d-Galf-(1→4)-d-GlcNAc with a donor derivative of β-d-Galp-(1→3)-d-Galp. The trichloroacetimidate method, as

  游离β-d-Gal的合成p（1→3）-β-d-Gal的- p - （1→6） - [β-d-Gal的˚F - （1→4）] - d-GlcNAc的和描述了先前已经通过还原性β-消除克氏锥虫糖蛋白分离的相应的糖醇。会聚路径通过冷凝β-d-Gal的的受体衍生物设想˚F - （1→4）-D-GlcNAc的具有β-d-Gal的供体衍生物p - （1→3）-D-半乳糖p。三氯乙酰亚胺酸盐方法以及SnCl 4促进的缩合用于引入半乳糖呋喃糖基单元。另一方面，用糖基-醛糖内酯方法，然后用二异戊基硼烷还原内酯，再异构化为半乳糖吡喃糖构型，得到供体衍生物，其通过三氯乙酰亚氨酸酯方法缩合。此外，对于引入β-d-Gal的的合成子p - （1→3）-D-半乳糖˚F单元进行说明。
• Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase
  作者：Verónica M. Mendoza、Rosalía Agusti、Carola Gallo-Rodriguez、Rosa M. de Lederkremer

  DOI：10.1016/j.carres.2006.03.033

  日期：2006.7

  The mucin-like glycoproteins of Trypanosoma cruzi have novel O-linked oligosaccharides that are acceptors of sialic acid in the trans-sialidase (TcTS) reaction. The transference of sialic acid from host glycoconjugates to the mucins is involved in infection and pathogenesis. The synthesis of the pentasaccharide, beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 43)]-beta-D-Galp-(1 -> 6)-[beta-D-Galf-(1 -> 4)]-D-GlcpNAc and the corresponding alditol, previously isolated by reductive beta-elimination of the mucins, is described. The key step was the 6-O-glycosylation of a easily accessible derivative of beta-D-Galf-(1 -> 4)-D-GlcpNAc with a beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 3)]-D-Galp donor using the trichloroacetimidate method. The P-linkage was diastereoselectively obtained by the nitrile effect. The pentasaccharide is the major oligosaccharide in the mucins of T. cruzi, G strain and presents two terminal beta-D-Galp residues for possible sialylation by TcTS. A preparative sialylation reaction was performed with its benzyl glycoside and the sialylated product was isolated and characterized. NMR spectroscopic analysis showed that selective monosialylation occurred at the terminal (1 -> 3) linked galactopyranose. (c) 2006 Elsevier Ltd. All rights reserved.