O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl)trichloroacetimidate | 1219002-98-8

• 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: O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl)trichloroacetimidate
• CAS: 1219002-98-8
• 化学式: C₆₃H₅₀Cl₃NO₁₈
• 分子量: 1215.44
• InChiKey: BAEWROAYKAKBLK-NXYSAQJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.03
• 重原子数：
  85.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  244.87
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->2)-3,5,6-tri-O-benzoyl-β-D-galactofuranosyl)trichloroacetimidate 、 benzyl 2-acetamido-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 73.0h， 以13%的产率得到2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->2)-3,5,6-tri-O-benzoyl-N-trichloroacetyl-β-D-galactofuranosylamine
  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：

  2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->2)-3,5,6-tri-O-benzoyl-α,β-D-galactofuranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以10%的产率得到O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->2)-3,5,6-tri-O-benzoyl-α-D-galactofuranosyl)trichloroacetimidate
  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