benzyl β-D-galactofuranosyl-(1->2)-β-D-galactofuranosyl-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranoside | 1219003-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl β-D-galactofuranosyl-(1->2)-β-D-galactofuranosyl-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranoside
• CAS: 1219003-11-8
• 化学式: C₂₇H₄₁NO₁₆
• 分子量: 635.62
• InChiKey: WADBVDRRNYOZDW-LLEBQHLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  266.55
• 氢给体数：
  10.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  benzyl β-D-galactofuranosyl-(1->2)-β-D-galactofuranosyl-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 20.0h， 生成 β-D-galactofuranosyl-(1->2)-β-D-galactofuranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 、 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-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