[(2S,3R,4R,5S)-4-benzoyloxy-6-bromo-2-methyl-5-phenylmethoxyoxan-3-yl] benzoate | 327593-98-6

• 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: [(2S,3R,4R,5S)-4-benzoyloxy-6-bromo-2-methyl-5-phenylmethoxyoxan-3-yl] benzoate
• CAS: 327593-98-6
• 化学式: C₂₇H₂₅BrO₆
• 分子量: 525.396
• InChiKey: GJJJQTYZDSEVFW-WRGQOZACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5S)-4-benzoyloxy-6-bromo-2-methyl-5-phenylmethoxyoxan-3-yl] benzoate 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 氰化汞 、 mercury dibromide 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 31.0h， 生成 propyl 2,3-di-O-(α-L-fucopyranosyl)-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
• 作为产物：
  描述：

  3,4-di-O-benzoyl-2-O-benzyl-α,β-L-fucopyranose 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2S,3R,4R,5S)-4-benzoyloxy-6-bromo-2-methyl-5-phenylmethoxyoxan-3-yl] benzoate
  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. III. EFFECT OF BENZOYL GROUP AT O-3 ON STEREOSELECTIVITY OF GLYCOSYLATION BY 3-<i>O</i>- AND 3,4-DI-<i>O</i>-BENZOYLATED 2-<i>O</i>-BENZYLFUCOSYL BROMIDES
  作者：Alexey G. Gerbst、Nadezhda E. Ustuzhanina、Alexey A. Grachev、Elena A. Khatuntseva、Dmitry E. Tsvetkov、Dennis M. Whitfield、Attila Berces、Nikolay E. Nifantiev

  DOI：10.1081/car-100108659

  日期：2001.12.31

  The effect of a benzoyl group at O-3 on stereoselectivity of glycosylation by 3-O- and 3,4-di-O-benzoylated 2-O-benzyl-L-fucopyranosyl bromides was studied by direct chemical experiments and computational chemistry. The influence of a benzoyl group at O-3 of the fucosyl donors was shown to have a larger effect on the efficiency of α-fucosylation than a benzoyl group at O-4. It is hypothesized that

  通过直接化学实验和计算化学研究了在O-3处的苯甲酰基对3- O-和3,4-二-O-苯甲酰化的2 - O-苄基-L-呋喃核糖基溴化物的糖基化的立体选择性的影响。已显示，在岩藻糖基供体的O-3上，苯甲酰基对α-岩藻糖基化效率的影响大于在O-4上的苯甲酰基。据推测，这是由于O-3处的苯甲酰基参与糖基阳离子稳定化的能力的结果。
• 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.