methyl 4,5,7-tri-O-benzyl-α-D-glycero-D-talo-septanoside | 946416-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,5,7-tri-O-benzyl-α-D-glycero-D-talo-septanoside
• 英文别名: (2S,3S,4R,5R,6R,7R)-2-methoxy-5,6-bis(phenylmethoxy)-7-(phenylmethoxymethyl)oxepane-3,4-diol
• CAS: 946416-36-0
• 化学式: C₂₉H₃₄O₇
• 分子量: 494.585
• InChiKey: UFSGCPBLWIDWDE-MRMYXZNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4,5,7-tri-O-benzyl-α-D-glycero-D-talo-septanoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以89%的产率得到methyl α-D-glycero-D-talo-septanoside
  参考文献：
  名称：

  Synthesis of Septanosides through an Oxyglycal Route

  摘要：

  A new route to synthesize septanoside derivatives from protected 2-hydroxyglycals is reported. Ring expansion of a pyranoside to a septanoside was achieved through key reactions of a cyclopropanation, ring opening, oxidation, and reduction. Methyl septanoside derivatives, namely, methyl alpha-D-glycero-D-talo-septanoside and methyl alpha-D-glycero-L-altro-septanoside, were synthesized in an overall yield of 35% and 46%, respectively, from the corresponding protected 2-hydroxy glycals.

  DOI：

  10.1021/jo070444e
• 作为产物：
  描述：

  methyl 2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-enoseptanoside 在 Oxone 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.0h， 生成 methyl 4,5,7-tri-O-benzyl-α-D-glycero-D-talo-septanoside
  参考文献：
  名称：

  Synthesis of Septanosides through an Oxyglycal Route

  摘要：

  A new route to synthesize septanoside derivatives from protected 2-hydroxyglycals is reported. Ring expansion of a pyranoside to a septanoside was achieved through key reactions of a cyclopropanation, ring opening, oxidation, and reduction. Methyl septanoside derivatives, namely, methyl alpha-D-glycero-D-talo-septanoside and methyl alpha-D-glycero-L-altro-septanoside, were synthesized in an overall yield of 35% and 46%, respectively, from the corresponding protected 2-hydroxy glycals.

  DOI：

  10.1021/jo070444e