allyl 3-O-(3-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside | 488719-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-(3-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside
• 英文别名: Bn(-2)[Bz(-3)]Fuc(a1-3)[Bn(-2)]Fuc(a)-O-allyl；[(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] benzoate
• CAS: 488719-75-1
• 化学式: C₃₆H₄₂O₁₀
• 分子量: 634.723
• InChiKey: FCRCGHYVNUPRGQ-INBHNLTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  allyl 3-O-(3-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside 在 pyridine-SO3 complex 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Benzoic acid (2S,3S,4S,5R,6S)-2-((2R,3S,4S,5R,6S)-2-allyloxy-3-benzyloxy-6-methyl-5-sulfooxy-tetrahydro-pyran-4-yloxy)-3-benzyloxy-6-methyl-5-sulfooxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  SYNTHESIS, NMR, AND CONFORMATIONAL STUDIES OF FUCOIDAN FRAGMENTS 4: 4-MONO- AND 4,4′-DISULFATED (1→3)-α-l-FUCOBIOSIDE AND 4-SULFATED FUCOSIDE FRAGMENTS

  摘要：

  Propyl 4-O-sulfonato- and 4,4'-di-O-sulfonato-3-O-alpha-L-fucopyranosyl-alpha-L-fucopyranosides, which are related to fragments of brown algal fucoidans, have been synthesized. Their spectral (H-1 and C-13 NMR, NOE) and conformational properties have been studied in combination with molecular modeling and compared with the respective non-sulfated propyl fucobioside. Correlations between chemical shifts and conformational properties of these compounds were investigated.

  DOI：

  10.1081/car-120013500
• 作为产物：
  描述：

  sodium;[(2S,3R,4S,5S,6R)-4-[(2S,3S,4R,5R,6S)-4,5-dibenzoyloxy-6-methyl-3-phenylmethoxyoxan-2-yl]oxy-2-methyl-5-phenylmethoxy-6-prop-2-enoxyoxan-3-yl] sulfate 在 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.0h， 生成 allyl 3-O-(3-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside
  参考文献：
  名称：

  SYNTHESIS, NMR, AND CONFORMATIONAL STUDIES OF FUCOIDAN FRAGMENTS 4: 4-MONO- AND 4,4′-DISULFATED (1→3)-α-l-FUCOBIOSIDE AND 4-SULFATED FUCOSIDE FRAGMENTS

  摘要：

  Propyl 4-O-sulfonato- and 4,4'-di-O-sulfonato-3-O-alpha-L-fucopyranosyl-alpha-L-fucopyranosides, which are related to fragments of brown algal fucoidans, have been synthesized. Their spectral (H-1 and C-13 NMR, NOE) and conformational properties have been studied in combination with molecular modeling and compared with the respective non-sulfated propyl fucobioside. Correlations between chemical shifts and conformational properties of these compounds were investigated.

  DOI：

  10.1081/car-120013500

文献信息

• SYNTHESIS, NMR, AND CONFORMATIONAL STUDIES OF FUCOIDAN FRAGMENTS 4: 4-MONO- AND 4,4′-DISULFATED (1→3)-α-<scp>l</scp>-FUCOBIOSIDE AND 4-SULFATED FUCOSIDE FRAGMENTS
  作者：Alexey G. Gerbst、Nadezhda E. Ustuzhanina、Alexey A. Grachev、Natalya S. Zlotina、Elena A. Khatuntseva、Dmitry E. Tsvetkov、Alexander S. Shashkov、Anatoly I. Usov、Nikolay E. Nifantiev

  DOI：10.1081/car-120013500

  日期：2002.9.23

  Propyl 4-O-sulfonato- and 4,4'-di-O-sulfonato-3-O-alpha-L-fucopyranosyl-alpha-L-fucopyranosides, which are related to fragments of brown algal fucoidans, have been synthesized. Their spectral (H-1 and C-13 NMR, NOE) and conformational properties have been studied in combination with molecular modeling and compared with the respective non-sulfated propyl fucobioside. Correlations between chemical shifts and conformational properties of these compounds were investigated.