methyl 6-O-[(2-azidomethyl)phenylacetyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 428500-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-[(2-azidomethyl)phenylacetyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl 2-[2-(azidomethyl)phenyl]acetate
• CAS: 428500-96-3
• 化学式: C₃₇H₃₉N₃O₇
• 分子量: 637.733
• InChiKey: HQNZHEGJBPWSQO-VDLPFXIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  methyl 6-O-[(2-azidomethyl)phenylacetyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷
  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 methyl 6-O-[(2-azidomethyl)phenylacetyl]-2,3,4-tri-O-benzyl-α-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

文献信息

• (2-Azidomethyl)phenylacetyl as a new, reductively cleavable protecting group for hydroxyl groups in carbohydrate synthesis
  作者：Jinghua Xu、Zhongwu Guo

  DOI：10.1016/s0008-6215(01)00292-0

  日期：2002.2

  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.