allyl 3-O-(2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside | 488719-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-(2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside
• 英文别名: Bn(-2)Fuc(a1-3)[Bn(-2)]Fuc(a)-O-allyl；(2S,3S,4R,5S,6S)-6-[(2S,3R,4R,5S,6R)-3-hydroxy-2-methyl-5-phenylmethoxy-6-prop-2-enoxyoxan-4-yl]oxy-2-methyl-5-phenylmethoxyoxane-3,4-diol
• CAS: 488719-74-0
• 化学式: C₂₉H₃₈O₉
• 分子量: 530.615
• InChiKey: VSWRAZDCVFJJAX-CHMJNUDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 3-O-(2-O-benzyl-α-L-fucopyranosyl)-2-O-benzyl-α-L-fucopyranoside 在 (C₄H₉)2SnO 、 4 A molecular sieve 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 27.5h， 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
• 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 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到allyl 3-O-(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 of the Oligosaccharides Related to Branching Sites of Fucosylated Chondroitin Sulfates from Sea Cucumbers
  作者：Nadezhda Ustyuzhanina、Polina Fomitskaya、Alexey Gerbst、Andrey Dmitrenok、Nikolay Nifantiev

  DOI：10.3390/md13020770

  日期：——

  such as blood coagulation, thrombosis, angiogenesis, inflammation, bacterial and viral adhesion. To determine pharmacophore fragments in FCS we have started systematic synthesis of oligosaccharides with well-defined structure related to various fragments of these polysaccharides. In this communication, the synthesis of non-sulfated and selectively O-sulfated di- and trisaccharides structurally related

  如今，来自海参的天然阴离子多糖岩藻糖基化硫酸软骨素（FCS）由于具有影响各种生物过程的能力而备受关注，例如血液凝固，血栓形成，血管生成，炎症，细菌和病毒粘附。为了确定FCS中的药效基团片段，我们已经开始系统地合成具有与这些多糖的各种片段相关的结构明确的寡糖。在这种交流中，描述了与FCS分支位点结构相关的非硫酸化和选择性O硫酸化的二糖和三糖的合成。目标化合物由在O-3α-1-岩藻糖基或α-1-岩藻糖基-（1→3）-α-1-岩藻糖基取代基处的丙基β-d-葡萄糖醛酸残基组成。根据迄今已知的全人类FCS结构选择合成靶的岩藻糖单位中的O-硫酸化模式。使用2-O-苄基-3,4-二-O-氯乙酰基-α-1-岩藻糖基三氯乙酰亚氨酸酯作为供体，实现了立体特异性α-糖苷键的形成。糖基化的立体化学结果可通过氯乙酰基的远程参与形成稳定的糖基阳离子来解释，该稳定的糖基阳离子仅可从α侧受到糖基受体的攻击。实验结果与SCF
• 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.
• 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.