1,5-anhydro-2,3,4,6-tetra-O-benzyl-1,2-C-(dichloromethylene)-α-D-glycero-L-altro-hexitol | 946416-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,3,4,6-tetra-O-benzyl-1,2-C-(dichloromethylene)-α-D-glycero-L-altro-hexitol
• 英文别名: (1S,3R,4S,5S,6S)-7,7-dichloro-4,5,6-tris(phenylmethoxy)-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptane
• CAS: 946416-39-3
• 化学式: C₃₅H₃₄Cl₂O₅
• 分子量: 605.558
• InChiKey: PKIMMRJOPVOKEG-OWIQAHIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,3,4,6-tetra-O-benzyl-1,2-C-(dichloromethylene)-α-D-glycero-L-altro-hexitol 在 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 1,4-二氧六环 、 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 58.0h， 生成 methyl 4,5,7-tri-O-benzyl-α-D-glycero-L-altro-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：

  氯仿 、 2,3,4,6-tetra-O-benzyl-D-galactal 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 反应 2.0h， 以85%的产率得到1,5-anhydro-2,3,4,6-tetra-O-benzyl-1,2-C-(dichloromethylene)-α-D-glycero-L-altro-hexitol
  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