methyl 2,3,4-tri-O-acetyl-6-O-[(2-azidomethyl)phenylacetyl]-α-D-glucopyranoside | 428500-98-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-O-[(2-azidomethyl)phenylacetyl]-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methyl 2-[2-(azidomethyl)phenyl]acetate
• CAS: 428500-98-5
• 化学式: C₂₂H₂₇N₃O₁₀
• 分子量: 493.47
• InChiKey: FSEGMTVEEDTYSD-VOFPXKNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-[(2-azidomethyl)phenylacetyl]-α-D-glucopyranoside 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以81%的产率得到methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose
  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：

  ethyl (2-azidomethyl)phenylacetate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 methyl 2,3,4-tri-O-acetyl-6-O-[(2-azidomethyl)phenylacetyl]-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