dimethyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate | 1295541-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-dimethoxyphosphoryl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 1295541-53-5
• 化学式: C₃₁H₃₈NO₈P
• 分子量: 583.618
• InChiKey: GNTFZCOGAVWJSY-CWMPKMHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 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：

  dimethyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosylphosphonate 在 Raney Ni/Pt 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 24.0h， 生成 dimethyl 2-acetamido-3,4,6-tri-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