3-O-(2-azidomethyl)phenylacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 428500-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(2-azidomethyl)phenylacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 2-[2-(azidomethyl)phenyl]acetate
• CAS: 428500-97-4
• 化学式: C₂₁H₂₇N₃O₇
• 分子量: 433.461
• InChiKey: BZKHMRGOTPYAQW-IQZDNPOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-O-(2-azidomethyl)phenylacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 28.0h， 以80%的产率得到3-O-(2-azidomethyl)phenylacetyl-1,2-O-isopropylidene-α-D-glucofuranose
  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 、 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 8.5h， 生成 3-O-(2-azidomethyl)phenylacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  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