(1S,3R,4R,5S,6S)-7,7-dichloro-5,6-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-oxabicyclo[4.1.0]heptane | 1202532-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R,5S,6S)-7,7-dichloro-5,6-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-oxabicyclo[4.1.0]heptane
• CAS: 1202532-59-9
• 化学式: C₆₂H₆₂Cl₂O₁₀
• 分子量: 1038.07
• InChiKey: USMDDEMBQDCIDC-KQLVBHNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  74
• 可旋转键数：
  25
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5S,6S)-7,7-dichloro-5,6-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-oxabicyclo[4.1.0]heptane 、 sodium methylate 在 甲醇 作用下， 以 甲苯 为溶剂， 反应 120.0h， 以38%的产率得到(2R,3R,4S,7S)-6-chloro-7-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2,3,4,7-tetrahydrooxepine
  参考文献：
  名称：

  Ring Expansion of Oxyglycals. Synthesis and Conformational Analysis of Septanoside-Containing Trisaccharides

  摘要：

  Oxyglycals, derived from lactose and maltose, were expanded to trisaccharides through a ring expansion method. Trisaccharides with 6-7-5 and 6-7-6 ring sizes were prepared through the ring expansion method, with high diastereoselectivities, in each step of their synthesis. The NOE and ROESY NMR spectroscopies were used to assess the dipolar Couplings within the trisaccharide. A computational study was undertaken, from which low energy conformations, as well as, dihedral angles that define the glycosidic linkages were identified.

  DOI：

  10.1021/jo901945e
• 作为产物：
  描述：

  氯仿 、 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以75%的产率得到(1S,3R,4R,5S,6S)-7,7-dichloro-5,6-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-oxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Ring Expansion of Oxyglycals. Synthesis and Conformational Analysis of Septanoside-Containing Trisaccharides

  摘要：

  Oxyglycals, derived from lactose and maltose, were expanded to trisaccharides through a ring expansion method. Trisaccharides with 6-7-5 and 6-7-6 ring sizes were prepared through the ring expansion method, with high diastereoselectivities, in each step of their synthesis. The NOE and ROESY NMR spectroscopies were used to assess the dipolar Couplings within the trisaccharide. A computational study was undertaken, from which low energy conformations, as well as, dihedral angles that define the glycosidic linkages were identified.

  DOI：

  10.1021/jo901945e

文献信息

• Ring Expansion of Oxyglycals. Synthesis and Conformational Analysis of Septanoside-Containing Trisaccharides
  作者：N. Vijaya Ganesh、S. Raghothama、R. Sonti、N. Jayaraman

  DOI：10.1021/jo901945e

  日期：2010.1.1

  Oxyglycals, derived from lactose and maltose, were expanded to trisaccharides through a ring expansion method. Trisaccharides with 6-7-5 and 6-7-6 ring sizes were prepared through the ring expansion method, with high diastereoselectivities, in each step of their synthesis. The NOE and ROESY NMR spectroscopies were used to assess the dipolar Couplings within the trisaccharide. A computational study was undertaken, from which low energy conformations, as well as, dihedral angles that define the glycosidic linkages were identified.