methyl (2S)-2-[(2S,4R,5R,6S)-5-acetyloxy-4-[(1S)-1,2-diacetyloxyethyl]-4-hydroxy-6-methoxyoxan-2-yl]-2-(4-methylphenyl)sulfonyloxyacetate | 1042438-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2S)-2-[(2S,4R,5R,6S)-5-acetyloxy-4-[(1S)-1,2-diacetyloxyethyl]-4-hydroxy-6-methoxyoxan-2-yl]-2-(4-methylphenyl)sulfonyloxyacetate
• CAS: 1042438-93-6
• 化学式: C₂₄H₃₂O₁₄S
• 分子量: 576.576
• InChiKey: HSYXKEWOARVNKC-IFQWMDHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  196
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(2S,4R,5R,6S)-5-acetyloxy-4-[(1S)-1,2-diacetyloxyethyl]-4-hydroxy-6-methoxyoxan-2-yl]-2-(4-methylphenyl)sulfonyloxyacetate 、 乙酸酐 在 硫酸 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 以60%的产率得到methyl 1,2,3-tri-O-acetyl-3-C-[(1S)-1,2-bis(acetyloxy)ethyl]-4-deoxy-6-O-tosyl-α-D-allo-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：

  、 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 为溶剂， 反应 44.0h， 以89%的产率得到methyl (2S)-2-[(2S,4R,5R,6S)-5-acetyloxy-4-[(1S)-1,2-diacetyloxyethyl]-4-hydroxy-6-methoxyoxan-2-yl]-2-(4-methylphenyl)sulfonyloxyacetate
  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