methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-acetamido-D-gluconate | 1295541-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-acetamido-D-gluconate
• 英文别名: methyl (2R,3S,4R,5S,6R)-5-acetamido-6-dimethoxyphosphoryl-3,4-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 1295541-48-8
• 化学式: C₂₅H₃₂NO₉P
• 分子量: 521.504
• InChiKey: DEXFOESBQCUUII-ZFAFIAQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-acetamido-D-gluconate 在 palladium on carbon 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 3.0h， 生成
  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：

  3,4-di-O-benzyl-D-glucal 在 sodium hypochlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 硝酸乙酸酐 、 Raney Ni/Pt 、 氢气 、 potassium hydrogencarbonate 、 戴斯-马丁氧化剂 、 三乙胺 、 sodium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， -33.0~20.0 ℃ 、310.27 kPa 条件下， 反应 78.5h， 生成 methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-acetamido-D-gluconate
  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

文献信息

• Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals
  作者：Beenu Bhatt、Robin J. Thomson、Mark von Itzstein

  DOI：10.1021/jo2002193

  日期：2011.5.20

  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.