5-aminopentyl [2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl]-(1->3)-[α-D-mannopyranosyl]-(1->6)-β-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 1319152-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-aminopentyl [2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl]-(1->3)-[α-D-mannopyranosyl]-(1->6)-β-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6R)-2-[(2S,3S,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6R)-5-acetamido-6-(5-aminopentoxy)-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1319152-78-7
• 化学式: C₄₇H₈₂N₄O₃₁
• 分子量: 1199.18
• InChiKey: WXAOOHQFTISODT-WRVWWIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.5
• 重原子数：
  82
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  548
• 氢给体数：
  20
• 氢受体数：
  32

反应信息

• 作为产物：
  描述：

  在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以69%的产率得到5-aminopentyl [2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl]-(1->3)-[α-D-mannopyranosyl]-(1->6)-β-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure

  摘要：

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.006