methyl [(dimethylphosphonyl) 2-acetamido-3,4-di-O-benzyl-1,2-dideoxy-β-D-glucopyranosid]uronate | 1295541-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [(dimethylphosphonyl) 2-acetamido-3,4-di-O-benzyl-1,2-dideoxy-β-D-glucopyranosid]uronate
• 英文别名: methyl (6S)-5-acetamido-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-L-gulonate；methyl (2S,3S,4R,5R,6S)-5-acetamido-6-dimethoxyphosphoryl-3,4-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 1295541-59-1
• 化学式: C₂₅H₃₂NO₉P
• 分子量: 521.504
• InChiKey: DEXFOESBQCUUII-BZDYCCQFSA-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 [(dimethylphosphonyl) 2-acetamido-3,4-di-O-benzyl-1,2-dideoxy-β-D-glucopyranosid]uronate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Uronosyl phosphonate-based sialidase inhibitor synthesis and conformational analysis

  摘要：

  With a view to development of novel sialidase inhibitors, mimetics of the natural inhibitor Neu5Ac2en have been prepared in which a phosphonate group replaces the sialic acid glycerol side chain. Different hex-4-en derivatives adopt half-chair conformations that place the glycosyl phosphonate in an equatorial position. For the alpha-L-threo-hex-4-en derivative this conformation is equivalent to that of Neu5Ac2en, and opposite to that seen for alkyl O-glycosides with the same overall stereochemistry. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.015
• 作为产物：
  描述：

  dimethyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosylphosphonate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 氯化亚砜 、 三氟甲磺酸三甲基硅酯 、 四丁基溴化铵 、 sodium methylate 、 碳酸氢钠 、 sodium chloride 、 potassium bromide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.5h， 生成 methyl [(dimethylphosphonyl) 2-acetamido-3,4-di-O-benzyl-1,2-dideoxy-β-D-glucopyranosid]uronate
  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