methyl 1,2,3-tri-O-acetyl-6-azido-3-C-[(1S)-1,2-bis(acetyloxy)ethyl]-4,6-dideoxy-β-L-ido-heptopyranuronate | 1042438-98-1

• 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 1,2,3-tri-O-acetyl-6-azido-3-C-[(1S)-1,2-bis(acetyloxy)ethyl]-4,6-dideoxy-β-L-ido-heptopyranuronate
• 英文别名: methyl (2R)-2-azido-2-[(2S,4R,5R,6R)-4,5,6-triacetyloxy-4-[(1S)-1,2-diacetyloxyethyl]oxan-2-yl]acetate
• CAS: 1042438-98-1
• 化学式: C₂₀H₂₇N₃O₁₃
• 分子量: 517.447
• InChiKey: PNSNISSQLIXVAQ-JMCXLBPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  181
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 1,2,3-tri-O-acetyl-6-azido-3-C-[(1S)-1,2-bis(acetyloxy)ethyl]-4,6-dideoxy-β-L-ido-heptopyranuronate 、 乙酸酐 在 palladium on activated charcoal 氢气 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 以92%的产率得到methyl 6-C-acetamido-1,2,3-tri-O-acetyl-3-C-[(1S)-1,2-bis(acetyloxy)ethyl]-4,6-dideoxy-β-L-ido-heptopyranuronate
  参考文献：
  名称：

  Synthetic Studies on the Carbohydrate Moiety of Amipurimycin

  摘要：

  The carbohydrate core of amipurimycin in its fully acetylated form was synthesized in 24 steps starting from commercially available methyl 4,6-O-benzylidene--D-glucopyranoside to give an overall yield of 1.5%. The late-stage intermediates involved were suitable for total synthesis of amipurimycin. It was further discovered that the branches and the protecting groups on the sugar rings of involved intermediates had a significant influence on their conformations, which in turn resulted in new and interesting cyclization reactions.

  DOI：

  10.1080/07328300802030787
• 作为产物：
  描述：

  methyl 1,2,3-tri-O-acetyl-3-C-[(1S)-1,2-bis(acetyloxy)ethyl]-4-deoxy-6-O-tosyl-α-D-gluco-heptopyranuronate 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到methyl 1,2,3-tri-O-acetyl-6-azido-3-C-[(1S)-1,2-bis(acetyloxy)ethyl]-4,6-dideoxy-β-L-ido-heptopyranuronate
  参考文献：
  名称：

  Synthetic Studies on the Carbohydrate Moiety of Amipurimycin

  摘要：

  The carbohydrate core of amipurimycin in its fully acetylated form was synthesized in 24 steps starting from commercially available methyl 4,6-O-benzylidene--D-glucopyranoside to give an overall yield of 1.5%. The late-stage intermediates involved were suitable for total synthesis of amipurimycin. It was further discovered that the branches and the protecting groups on the sugar rings of involved intermediates had a significant influence on their conformations, which in turn resulted in new and interesting cyclization reactions.

  DOI：

  10.1080/07328300802030787