dimethyl 2-acetamido-6-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate | 1295541-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2-acetamido-6-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-6-dimethoxyphosphoryl-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 1295541-55-7
• 化学式: C₂₆H₃₄NO₉P
• 分子量: 535.531
• InChiKey: PUEPQOVRQAUZFB-SDVOOXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl 2-acetamido-6-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以0.6 g的产率得到dimethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate
  参考文献：
  名称：

  Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals

  摘要：

  Two approaches are described for the synthesis of 2-acylamino uronic acid glycosyl phosphonates from readily accessible D-glucal. The first approach that entailed oxidation of the C-6 hydroxyl group followed by phosphonylation of the uronate 2-nitro-glycal, resulted in the formation of the beta-L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the beta-D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.

  DOI：

  10.1021/jo2002193
• 作为产物：
  描述：

  在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 dimethyl 2-acetamido-6-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate
  参考文献：
  名称：

  Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals

  摘要：

  Two approaches are described for the synthesis of 2-acylamino uronic acid glycosyl phosphonates from readily accessible D-glucal. The first approach that entailed oxidation of the C-6 hydroxyl group followed by phosphonylation of the uronate 2-nitro-glycal, resulted in the formation of the beta-L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the beta-D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.

  DOI：

  10.1021/jo2002193