(3S,4R,5R,6S)-3,6-bis(benzyloxy)octa-1,7-diene-4,5-diol | 671205-17-7

• 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: (3S,4R,5R,6S)-3,6-bis(benzyloxy)octa-1,7-diene-4,5-diol
• 英文别名: (3S,4R,5R,6S)-3,6-Bis(benzyloxy)octa-1,7-diene-4,5-diol；(3S,4R,5R,6S)-3,6-bis(phenylmethoxy)octa-1,7-diene-4,5-diol
• CAS: 671205-17-7
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: ILUDXKLKWQXIOJ-CMOCDZPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6S)-3,6-bis(benzyloxy)octa-1,7-diene-4,5-diol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以43%的产率得到(1R,2R,3R,4S)-1,4-Bis-benzyloxy-1-oxiranyl-hex-5-ene-2,3-diol
  参考文献：
  名称：

  A comparison of the ring conformational properties of two derivatives prepared from the same diene diacetate precursor

  摘要：

  Results of single-crystal X-ray experiments performed for the title compounds, (1S, 2R, 3S, 4R, 5R)-4-benzyloxy-2-[1-(benzyloxy) allyl]-5-hydroxymethyl-2,3,4,5-tetrahydrofuran-3-ol, C22H26O5, (I), and (3R, 5S, 6S, 7S, 8S)-3,6-bis(benzyloxy)-5-iodomethyl-2,3,4,5- tetrahydrofuro[3,2-b] furan-2-one, C21H21IO5, (II), demonstrate that the tetrahydrofuran ring that is common to both structures adopts a different conformation in each molecule. Structural analyses of (I) and (II), which were prepared from the same precursor, indicate that their different conformations are caused by hydrogen-bonding interactions in the case of (I) and the presence of a fused bicyclic ring system in the case of (II). Density functional theory calculations on simplified analogs of (I) and (II) are also presented.

  DOI：

  10.1107/s0108270103025757

文献信息

• A comparison of the ring conformational properties of two derivatives prepared from the same diene diacetate precursor
  作者：Ilia A. Guzei、Robert W. Clark、Steven D. Burke、William T. Lambert

  DOI：10.1107/s0108270103025757

  日期：2003.12.15

  Results of single-crystal X-ray experiments performed for the title compounds, (1S, 2R, 3S, 4R, 5R)-4-benzyloxy-2-[1-(benzyloxy) allyl]-5-hydroxymethyl-2,3,4,5-tetrahydrofuran-3-ol, C22H26O5, (I), and (3R, 5S, 6S, 7S, 8S)-3,6-bis(benzyloxy)-5-iodomethyl-2,3,4,5- tetrahydrofuro[3,2-b] furan-2-one, C21H21IO5, (II), demonstrate that the tetrahydrofuran ring that is common to both structures adopts a different conformation in each molecule. Structural analyses of (I) and (II), which were prepared from the same precursor, indicate that their different conformations are caused by hydrogen-bonding interactions in the case of (I) and the presence of a fused bicyclic ring system in the case of (II). Density functional theory calculations on simplified analogs of (I) and (II) are also presented.