2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside | 1000813-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS: 1000813-65-9
• 化学式: C₃₅H₃₂N₂O₁₂
• 分子量: 672.645
• InChiKey: COAUJYXIJMESLM-GLPBNNEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  167.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 反应 20.0h， 以95%的产率得到methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  4,6‐O‐Benzylidene Directed β‐Mannosylation Without Intermediate Triflate Formation? Comparison of Trichloroacetimidate and DISAL Donors in Microwave‐Promoted Glycosylations under Neutral Conditions

  摘要：

  4,6-Benzylidene-protected marmosyl donors have emerged as efficient tools for the formation of 1,2-cis beta-mannosides, which otherwise are difficult to access. Previously studied sulfoxide and trichloroacetimidate mannosyl donors were activated with strong Lewis acids at low temperature and the glycosylations are believed to proceed through intermediate formation of an a-triflate. This paper describes the synthesis of new benzylidene-protected glucosyl and marmosyl methyl 3,5-dinitrosalicylate (DISAL) donors, their application in O-glycosylations, and comparison with a mannosyl trichloroacetimidate donor. In contrast to previous reports on torsionally "disarmed" donors, these glycosylations were performed in the absence of strong Lewis acids, but in the presence of lithium perchlorate or triflate, using either conventional heating to 40 to 60 degrees C or precise microwave heating to 100 to 150 degrees C. This approach aimed at addressing the question of whether marmosyl triflate intermediates are essential for high P-selectivity in 4,6-O-benzylidene directed mannosylations. We find, again, that precise microwave heating promoted glycosylations under very mild conditions.

  DOI：

  10.1080/07328300701634762
• 作为产物：
  描述：

  2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose 、 methyl 2-fluoro-3,5-dinitrobenzoic ester 在 4-二甲氨基吡啶 、 lithium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 、 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  4,6‐O‐Benzylidene Directed β‐Mannosylation Without Intermediate Triflate Formation? Comparison of Trichloroacetimidate and DISAL Donors in Microwave‐Promoted Glycosylations under Neutral Conditions

  摘要：

  4,6-Benzylidene-protected marmosyl donors have emerged as efficient tools for the formation of 1,2-cis beta-mannosides, which otherwise are difficult to access. Previously studied sulfoxide and trichloroacetimidate mannosyl donors were activated with strong Lewis acids at low temperature and the glycosylations are believed to proceed through intermediate formation of an a-triflate. This paper describes the synthesis of new benzylidene-protected glucosyl and marmosyl methyl 3,5-dinitrosalicylate (DISAL) donors, their application in O-glycosylations, and comparison with a mannosyl trichloroacetimidate donor. In contrast to previous reports on torsionally "disarmed" donors, these glycosylations were performed in the absence of strong Lewis acids, but in the presence of lithium perchlorate or triflate, using either conventional heating to 40 to 60 degrees C or precise microwave heating to 100 to 150 degrees C. This approach aimed at addressing the question of whether marmosyl triflate intermediates are essential for high P-selectivity in 4,6-O-benzylidene directed mannosylations. We find, again, that precise microwave heating promoted glycosylations under very mild conditions.

  DOI：

  10.1080/07328300701634762