allyl 3-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranoside | 582322-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranoside
• 英文别名: Bn(-2)[Bz(-3)]Fuc(a1-3)[Bn(-2)]Fuc(a1-3)[Bn(-2)]Fuc(a)-O-allyl；[(2S,3S,4R,5R,6S)-5-hydroxy-2-[(2S,3S,4R,5R,6S)-5-hydroxy-2-[(2S,3R,4R,5S,6R)-3-hydroxy-2-methyl-5-phenylmethoxy-6-prop-2-enoxyoxan-4-yl]oxy-6-methyl-3-phenylmethoxyoxan-4-yl]oxy-6-methyl-3-phenylmethoxyoxan-4-yl] benzoate
• CAS: 582322-37-0
• 化学式: C₄₉H₅₈O₁₄
• 分子量: 870.991
• InChiKey: OYBYBJQUEFYIEE-NEOUAKHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  63
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  allyl 3-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranoside 在 三氧化硫吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 allyl 3-O-benzoyl-2-O-benzyl-4-O-sulfo-α-L-fucopyranosyl-(1->3)-2-O-benzyl-4-O-sulfo-α-L-fucopyranosyl-(1->3)-2-O-benzyl-4-O-sulfo-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis, NMR and Conformational Studies of Fucoidan Fragments. V.[1] Linear 4,4′,4″‐Tri‐O‐Sulfated and Parent Non‐sulfated (1→3)‐Fucotrioside Fragments

  摘要：

  Propyl 4,4',4"-tri-O-sulfated and non-sulfated (1 --> 3)-alpha-L-fucotriosides which are related to fragments of natural fucoidans have been synthesized. Their spectral and conformational properties have been investigated by H-1 and C-13 NMR, NOE and molecular modeling. Molecular mechanics calculations of the tri-O-sulfated compound as a trianion did not give agreement with the experimental NOE values, while the model with the non-dissociated sulfo group on the non-reducing end worked successfully. (1 --> 3)-Fucobioside fragments in both trisaccharides investigated were shown to have the same range of conformations as in previously described propyl (1 --> 3)-alpha-L-fucobiosides, but with the increase of the relative population of the conformer with the spatial proximity of H-1' and H-4 in the case of non-sulfated fucotrioside.

  DOI：

  10.1081/car-120020481
• 作为产物：
  描述：

  allyl 3,4-di-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranoside 在 (C₄H₉)2SnO 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 allyl 3-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis, NMR and Conformational Studies of Fucoidan Fragments. V.[1] Linear 4,4′,4″‐Tri‐O‐Sulfated and Parent Non‐sulfated (1→3)‐Fucotrioside Fragments

  摘要：

  Propyl 4,4',4"-tri-O-sulfated and non-sulfated (1 --> 3)-alpha-L-fucotriosides which are related to fragments of natural fucoidans have been synthesized. Their spectral and conformational properties have been investigated by H-1 and C-13 NMR, NOE and molecular modeling. Molecular mechanics calculations of the tri-O-sulfated compound as a trianion did not give agreement with the experimental NOE values, while the model with the non-dissociated sulfo group on the non-reducing end worked successfully. (1 --> 3)-Fucobioside fragments in both trisaccharides investigated were shown to have the same range of conformations as in previously described propyl (1 --> 3)-alpha-L-fucobiosides, but with the increase of the relative population of the conformer with the spatial proximity of H-1' and H-4 in the case of non-sulfated fucotrioside.

  DOI：

  10.1081/car-120020481

文献信息

• Synthesis, NMR and Conformational Studies of Fucoidan Fragments. V.[1] Linear 4,4′,4″‐Tri‐<i>O</i>‐Sulfated and Parent Non‐sulfated (1→3)‐Fucotrioside Fragments
  作者：Alexey G. Gerbst、Nadezhda E. Ustuzhanina、Alexey A. Grachev、Elena A. Khatuntseva、Dmitry E. Tsvetkov、Alexander S. Shashkov、Anatoly I. Usov、Marina E. Preobrazhenskaya、Natalya A. Ushakova、Nikolay E. Nifantiev

  DOI：10.1081/car-120020481

  日期：2003.1.5

  Propyl 4,4',4"-tri-O-sulfated and non-sulfated (1 --> 3)-alpha-L-fucotriosides which are related to fragments of natural fucoidans have been synthesized. Their spectral and conformational properties have been investigated by H-1 and C-13 NMR, NOE and molecular modeling. Molecular mechanics calculations of the tri-O-sulfated compound as a trianion did not give agreement with the experimental NOE values, while the model with the non-dissociated sulfo group on the non-reducing end worked successfully. (1 --> 3)-Fucobioside fragments in both trisaccharides investigated were shown to have the same range of conformations as in previously described propyl (1 --> 3)-alpha-L-fucobiosides, but with the increase of the relative population of the conformer with the spatial proximity of H-1' and H-4 in the case of non-sulfated fucotrioside.