p-methoxyphenyl 3-O-[(2-azidomethyl)phenylacetyl]-2-deoxy-2-phthalimido-β-D-glucopyranoside | 428500-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3-O-[(2-azidomethyl)phenylacetyl]-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-3-hydroxy-2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxan-4-yl] 2-[2-(azidomethyl)phenyl]acetate
• CAS: 428500-94-1
• 化学式: C₃₀H₂₈N₄O₉
• 分子量: 588.574
• InChiKey: QBFUTWVRCMJGBL-LYWSVWQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [2-(叠氮基甲基)苯基]乙酸 、 p-methoxyphenyl 3-O-[(2-azidomethyl)phenylacetyl]-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到p-methoxyphenyl 3,6-di-O-[(2-azidomethyl)phenylacetyl]-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  (2-Azidomethyl)phenylacetyl as a new, reductively cleavable protecting group for hydroxyl groups in carbohydrate synthesis

  摘要：

  The (2-azidomethyl)phenylacetyl group (AMPA) is described as a new protecting group for carbohydrates, AMPA was introduced to carbohydrate hydroxyl groups in the presence of DCC, while its removal was conveniently achieved via Lindlar catalyst-catalyzed hydrogenation that had no influence on other protecting groups including benzyl, acyl, acetal and ketal. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00292-0
• 作为产物：
  描述：

  邻甲苯基乙酸乙酯 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 9.5h， 生成 p-methoxyphenyl 3-O-[(2-azidomethyl)phenylacetyl]-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  (2-Azidomethyl)phenylacetyl as a new, reductively cleavable protecting group for hydroxyl groups in carbohydrate synthesis

  摘要：

  The (2-azidomethyl)phenylacetyl group (AMPA) is described as a new protecting group for carbohydrates, AMPA was introduced to carbohydrate hydroxyl groups in the presence of DCC, while its removal was conveniently achieved via Lindlar catalyst-catalyzed hydrogenation that had no influence on other protecting groups including benzyl, acyl, acetal and ketal. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00292-0