3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-4-O-chloroacetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 478182-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-4-O-chloroacetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(2R,3S,4R,5R,6S)-4-acetyloxy-6-[(2R,3S,4R,5R,6S)-4-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-2-[(4-methoxyphenyl)methoxymethyl]-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-2-[(4-methoxyphenyl)methoxymethyl]oxan-3-yl] 2-chloroacetate
• CAS: 478182-66-0
• 化学式: C₅₂H₄₉Cl₄N₃O₁₈
• 分子量: 1145.78
• InChiKey: YVFFPOIFUYJKDD-GEJXDKIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  77
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  251
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  烯丙醇 、 3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-4-O-chloroacetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 allyl 3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Preparation of orthogonally protected chitosan oligosaccharides: observation of an anomalous remote substituent effect

  摘要：

  Orthogonally protected chitosan tetrasaccharides were synthesized in a convergent fashion by trichloroacetimidate activation. The anomeric substituent at the reducing end of the disaccharide acceptor has a remarkably strong influence on glycosidic coupling; a thiophenyl-substituted disaccharide was observed to be an unusually poor glycosyl acceptor in comparison with the corresponding allyloxy-substituted disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00124-6
• 作为产物：
  描述：

  3-O-acetyl-4-O-chloroacetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.0h， 生成 3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-4-O-chloroacetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Preparation of orthogonally protected chitosan oligosaccharides: observation of an anomalous remote substituent effect

  摘要：

  Orthogonally protected chitosan tetrasaccharides were synthesized in a convergent fashion by trichloroacetimidate activation. The anomeric substituent at the reducing end of the disaccharide acceptor has a remarkably strong influence on glycosidic coupling; a thiophenyl-substituted disaccharide was observed to be an unusually poor glycosyl acceptor in comparison with the corresponding allyloxy-substituted disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00124-6