3-O-acetyl-4-O-chloroacetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 478182-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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-5-(1,3-dioxoisoindol-2-yl)-2-[(4-methoxyphenyl)methoxymethyl]-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 2-chloroacetate
• CAS: 478182-63-7
• 化学式: C₂₈H₂₆Cl₄N₂O₁₀
• 分子量: 692.334
• InChiKey: QFGINEFGARFRFK-ILRYNQFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  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 19.0h， 生成 phenyl 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-1-thio-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：

  氯乙酰氯 、 三氯乙腈 、 Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 水 、 丙酮 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-O-acetyl-4-O-chloroacetyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 、 Chloro-acetic acid (2R,3S,4R,5R,6S)-4-acetoxy-2-(3-bromo-4-methoxy-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
  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