2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-2-O-acetyl-3,6-di-O-benzoyl-β-D-galactofuranosyl trichloroacetimidate | 845533-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-2-O-acetyl-3,6-di-O-benzoyl-β-D-galactofuranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-5)][Bz(-6)]Galf(b1-5)[Bz(-3)][Bz(-6)]Galf2Ac(b)-O-C(NH)CCl3；[(2R)-2-[(2S,3S,4R,5S)-4-acetyloxy-3-benzoyloxy-5-(2,2,2-trichloroethanimidoyl)oxyoxolan-2-yl]-2-[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-[(1R)-1,2-dibenzoyloxyethyl]oxolan-2-yl]oxyethyl] benzoate
• CAS: 845533-42-8
• 化学式: C₅₈H₄₈Cl₃NO₁₈
• 分子量: 1153.37
• InChiKey: SNYPZBGDOQZBEV-UDJJGSHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  80
• 可旋转键数：
  28
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-2-O-acetyl-3,6-di-O-benzoyl-β-D-galactofuranosyl trichloroacetimidate 、 allyl 2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到allyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-3,6-di-O-benzoyl-2-O-acetyl-β-D-galactofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  First synthesis of the immunodominant β-galactofuranose-containing tetrasaccharide present in the cell wall of Aspergillus fumigatus

  摘要：

  beta-Galf-(1 --> 5)-p-Galf-(1 --> 6)-alpha-Manp-(1 --> 6)-alpha-Manp, the immunodominant epitope in the cell-wall galactomannan of Aspergillus fumigatus, was synthesized for the first time as its allyl glycoside. The key disaccharide glycosyl donor, 2,3,5,6-tetra- O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)-2-O-acetyl- 3,6-di-O-benzoyl-beta-D -galactofuranosyl trichloroacetimidate (10), was constructed by 5-O-glycosylation of 1,2-O-isopropylidene-3,6-di-O-benzoyl-alpha-D-galactofuranose (4) with 2,3,5,6-tetra-O-benzoyl-beta-galactofuranosyl trichloroacetimidate (5), followed by 1,2-O-deacetonation, acetylation, selective 1-O-deacetylation, and trichloroacetimidation. The target tetrasaccharide 16 was obtained by the condensation of allyl 2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside (14) as glycosyl acceptor with the disaccharide glycosyl donor 10, followed by deprotection. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.019
• 作为产物：
  描述：

  2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-3,6-di-O-benzoyl-1,2-O-isopropylidene-α-D-galactofuranose 在 potassium carbonate 、 苄胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 氯仿 为溶剂， 反应 50.0h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-2-O-acetyl-3,6-di-O-benzoyl-β-D-galactofuranosyl trichloroacetimidate
  参考文献：
  名称：

  First synthesis of the immunodominant β-galactofuranose-containing tetrasaccharide present in the cell wall of Aspergillus fumigatus

  摘要：

  beta-Galf-(1 --> 5)-p-Galf-(1 --> 6)-alpha-Manp-(1 --> 6)-alpha-Manp, the immunodominant epitope in the cell-wall galactomannan of Aspergillus fumigatus, was synthesized for the first time as its allyl glycoside. The key disaccharide glycosyl donor, 2,3,5,6-tetra- O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)-2-O-acetyl- 3,6-di-O-benzoyl-beta-D -galactofuranosyl trichloroacetimidate (10), was constructed by 5-O-glycosylation of 1,2-O-isopropylidene-3,6-di-O-benzoyl-alpha-D-galactofuranose (4) with 2,3,5,6-tetra-O-benzoyl-beta-galactofuranosyl trichloroacetimidate (5), followed by 1,2-O-deacetonation, acetylation, selective 1-O-deacetylation, and trichloroacetimidation. The target tetrasaccharide 16 was obtained by the condensation of allyl 2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside (14) as glycosyl acceptor with the disaccharide glycosyl donor 10, followed by deprotection. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.019