2,3,4,6-tetra-O-benzyl-1-deoxy-1,1-dipyrrylglucitol | 143542-03-4

• 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: 2,3,4,6-tetra-O-benzyl-1-deoxy-1,1-dipyrrylglucitol
• 英文别名: 2,3,4,6-Tetra-O-benzyl-1,1-dipyrryl-1-deoxy-D-glucitol；(2R,3R,4R,5S)-1,3,4,5-tetrakis(phenylmethoxy)-6,6-bis(1H-pyrrol-2-yl)hexan-2-ol
• CAS: 143542-03-4
• 化学式: C₄₂H₄₄N₂O₅
• 分子量: 656.822
• InChiKey: JPKCHRLMELIWRM-IMLWFBEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对氟苯甲醛 、 2,3,4,6-tetra-O-benzyl-1-deoxy-1,1-dipyrrylglucitol 在 三乙胺 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 5,15--10α,20β-porphyrin
  参考文献：
  名称：

  Synthesis and Characterization of Porphyrin-Sugar Carbon Conjugates

  摘要：

  The synthesis, structures, and spectroscopic properties of some 5,15-di-C-glycosyl-10,20-diarylporphyrins, representatives of a novel class of meso-C-glycoconjugated porphyrins, have been investigated. Porphyrins 9-14 were prepared in 6-16 % yield by condensation of suitable dipyrrylglycosides with aryl aldehydes in the presence of either trifluoroacetic acid or BF3 promoters. In all instances, alpha,beta-configured porphyrins were preferentially formed, alpha,alpha isomers being only marginal products. The UV-vis spectra in CHCl3 solution showed Soret bands which are red-shifted by about 20 nm as compared to the corresponding absorption maximum of the planar reference compound meso-5,15-bis(p-fluorophenyl)-10,20-diethylporphyrin (15). This suggested that the porphyrin macrocycles of 9-14 are inherently distorted to a significant extent. Detailed 1D and 2D H-1 NMR spectroscopic studies, including variable-temperature experiments in deuterated chloroform or tetrachloroethane, were carried out using the trans-disposed porphyrins 9 and 10. It was found that, at ambient temperature, these porphyrins adopted distorted saddle conformations in solution. Molecular mechanics techniques were used to analyze the distortion of porphyrin 9 as determined by the orientation of carbohydrate legs on the porphyrin periphery.

  DOI：

  10.1021/jo00086a035
• 作为产物：
  描述：

  吡咯 、 2,3,4,6-四苄基-D-吡喃葡萄糖 生成 2,3,4,6-tetra-O-benzyl-1-deoxy-1,1-dipyrrylglucitol
  参考文献：
  名称：

  吡咯C-糖缀合物的合成与转化

  摘要：

  对映体纯的开链α-pyrrylalditols 2，3，5和7个双核dipyrrylmethanes 8-10轴承手性alditolyl桥已经通过甘油的直接偶联合成1，阿拉伯糖4，和葡萄糖6与基于镁-钛金属吡咯试剂IV或镁铈III混合物。然后，单核和双核化合物被用作制备环状C-核苷类似物11-14或糖卟啉16的前体。

  DOI：

  10.1016/0040-4020(92)80012-5

文献信息

• Synthesis and transformation of pyrrole C-glycoconjugates
  作者：Giovanni Casiraghi、Mara Cornia、Gloria Rassu、Carlo Del Sante、Pietro Spanu

  DOI：10.1016/0040-4020(92)80012-5

  日期：1992.7

  chain α-pyrrylalditols 2, 3, 5 and 7 and dinuclear dipyrrylmethanes 8–10 bearing chiral alditolyl bridges have been synthesized by direct coupling of glyceraldehyde 1, arabinose 4, and glucose 6 with pyrrole metal reagents based on magnesium-titaniumIV or magnesium-ceriumIII blends. The mononuclear and dinuclear compounds were then exploited as precursors for the preparation of either cyclic C-nucleoside

  对映体纯的开链α-pyrrylalditols 2，3，5和7个双核dipyrrylmethanes 8-10轴承手性alditolyl桥已经通过甘油的直接偶联合成1，阿拉伯糖4，和葡萄糖6与基于镁-钛金属吡咯试剂IV或镁铈III混合物。然后，单核和双核化合物被用作制备环状C-核苷类似物11-14或糖卟啉16的前体。
• Synthesis and Characterization of Porphyrin-Sugar Carbon Conjugates
  作者：Giovanni Casiraghi、Mara Cornia、Franca Zanardi、Gloria Rassu、Enzio Ragg、Rita Bortolini

  DOI：10.1021/jo00086a035

  日期：1994.4

  The synthesis, structures, and spectroscopic properties of some 5,15-di-C-glycosyl-10,20-diarylporphyrins, representatives of a novel class of meso-C-glycoconjugated porphyrins, have been investigated. Porphyrins 9-14 were prepared in 6-16 % yield by condensation of suitable dipyrrylglycosides with aryl aldehydes in the presence of either trifluoroacetic acid or BF3 promoters. In all instances, alpha,beta-configured porphyrins were preferentially formed, alpha,alpha isomers being only marginal products. The UV-vis spectra in CHCl3 solution showed Soret bands which are red-shifted by about 20 nm as compared to the corresponding absorption maximum of the planar reference compound meso-5,15-bis(p-fluorophenyl)-10,20-diethylporphyrin (15). This suggested that the porphyrin macrocycles of 9-14 are inherently distorted to a significant extent. Detailed 1D and 2D H-1 NMR spectroscopic studies, including variable-temperature experiments in deuterated chloroform or tetrachloroethane, were carried out using the trans-disposed porphyrins 9 and 10. It was found that, at ambient temperature, these porphyrins adopted distorted saddle conformations in solution. Molecular mechanics techniques were used to analyze the distortion of porphyrin 9 as determined by the orientation of carbohydrate legs on the porphyrin periphery.