3,4-di-O-acetyl-6-O-[2-(azidomethyl)benzoyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 503180-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-acetyl-6-O-[2-(azidomethyl)benzoyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl 2-(azidomethyl)benzoate
• CAS: 503180-83-4
• 化学式: C₂₈H₂₄Cl₃N₅O₁₀
• 分子量: 696.885
• InChiKey: FUJDVKACANPYDV-OLROQXJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 3,4-di-O-acetyl-6-O-[2-(azidomethyl)benzoyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到3,4-di-O-acetyl-6-O-[2-(azidomethyl)benzoyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Toward the automated solid-phase synthesis of oligoglucosamines: systematic evaluation of glycosyl phosphate and glycosyl trichloroacetimidate building blocks

  摘要：

  Glucosamines are common components of many biologically important oligosaccharides. Reported is a systematic evaluation of glucosamine phosphates and trichloroacetimidates as glycosylating agents for the efficient construction of beta-(1 --> 6) glucosamine linkages. A set of differentially protected glucosamine donors incorporating a host of amine protecting groups, including 2-phthaloyl, benzyloxycarbonyl (Z), trichloroetheoxycarbonyl (Troc) and trichloroacetyl (TCA) protective groups. were prepared. Donors were initially evaluated for reactivity and protecting group compatibility in a solution-phase study with a model 6-hydroxyl galactose acceptor. Based on these results, glucosamine donor 10 was selected for the solution-phase synthesis of a beta-(1 --> 6)-glucosamine pentasaccharide. Finally, building block 10 proved well suited for use in the automated solid-phase synthesis of a repeating unit trisaccharide. An assessment of glucosamine phosphate donors as potential glycosylating agents for a variety of glucosamine linkages is also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00299-9
• 作为产物：
  描述：

  2-(azidomethyl)benzoyl chloride 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.08h， 生成 3,4-di-O-acetyl-6-O-[2-(azidomethyl)benzoyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Toward the automated solid-phase synthesis of oligoglucosamines: systematic evaluation of glycosyl phosphate and glycosyl trichloroacetimidate building blocks

  摘要：

  Glucosamines are common components of many biologically important oligosaccharides. Reported is a systematic evaluation of glucosamine phosphates and trichloroacetimidates as glycosylating agents for the efficient construction of beta-(1 --> 6) glucosamine linkages. A set of differentially protected glucosamine donors incorporating a host of amine protecting groups, including 2-phthaloyl, benzyloxycarbonyl (Z), trichloroetheoxycarbonyl (Troc) and trichloroacetyl (TCA) protective groups. were prepared. Donors were initially evaluated for reactivity and protecting group compatibility in a solution-phase study with a model 6-hydroxyl galactose acceptor. Based on these results, glucosamine donor 10 was selected for the solution-phase synthesis of a beta-(1 --> 6)-glucosamine pentasaccharide. Finally, building block 10 proved well suited for use in the automated solid-phase synthesis of a repeating unit trisaccharide. An assessment of glucosamine phosphate donors as potential glycosylating agents for a variety of glucosamine linkages is also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00299-9