allyl 3-O-(3,4-di-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside | 327594-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-(3,4-di-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside
• 英文别名: Bn(-2)[Bz(-3)][Bz(-4)]Fuc(a1-3)[Bn(-2)]Fuc(a)-O-allyl；[(2S,3R,4R,5S,6S)-4-benzoyloxy-6-[(2S,3R,4R,5S,6R)-3-hydroxy-2-methyl-5-phenylmethoxy-6-prop-2-enoxyoxan-4-yl]oxy-2-methyl-5-phenylmethoxyoxan-3-yl] benzoate
• CAS: 327594-02-5
• 化学式: C₄₃H₄₆O₁₁
• 分子量: 738.832
• InChiKey: DGTNAQJPBKLSFT-RPXZGUHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  54
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  allyl 3-O-(3,4-di-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 [(2S,3R,4R,5S,6S)-4-benzoyloxy-2-methyl-6-[(2S,3R,4S,5S,6R)-2-methyl-5-phenylmethoxy-6-prop-2-enoxy-3-sulfooxyoxan-4-yl]oxy-5-phenylmethoxyoxan-3-yl] benzoate
  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：

  allyl 3,4-O-isopropylidene-α-L-fucopyranoside 在 4 A molecular sieve 、 氰化汞 、 sodium hydride 、 三氟乙酸 、 mercury dibromide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.25h， 生成 allyl 3-O-(3,4-di-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 1:¹Desulfated 2,3- and 3,4-Branched Trisaccharide Fragments and Constituting Disaccharides

  摘要：

  Two fucotriosides with vicinal disubstitution alpha -L-Fuc-(1-->2)[alpha -L-Fuc-(1-->3)[alpha -L-Fuc-OPr (1) and alpha -L-Fuc-(1-->3)[alpha -L-Fuc-(1-->4)]alpha -L-Fuc-OPr (2), which are related to fragments of natural polysaccharides fucoidans, have been synthesized together with constituent disaccharides 3-5, Spectral and conformational properties of tri- and disaccharides have been investigated by (1)H, (13)C and NOE NMR spectroscopy.

  DOI：

  10.1080/07328300008544140

文献信息

• Synthesis, NMR and Conformational Studies of Fucoidan Fragments 1:¹Desulfated 2,3- and 3,4-Branched Trisaccharide Fragments and Constituting Disaccharides
  作者：Elena A. Khatuntseva、Nadezhda E. Ustuzhanina、Georgij V. Zatonskii、Alexander S. Shashkov、Anatoly I. Usov、Nikolay E. Nifant'ev

  DOI：10.1080/07328300008544140

  日期：2000.1.1

  Two fucotriosides with vicinal disubstitution alpha -L-Fuc-(1-->2)[alpha -L-Fuc-(1-->3)[alpha -L-Fuc-OPr (1) and alpha -L-Fuc-(1-->3)[alpha -L-Fuc-(1-->4)]alpha -L-Fuc-OPr (2), which are related to fragments of natural polysaccharides fucoidans, have been synthesized together with constituent disaccharides 3-5, Spectral and conformational properties of tri- and disaccharides have been investigated by (1)H, (13)C and NOE NMR spectroscopy.
• 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.