methyl (6S)-5-acetamido-2,6-anhydro-3,4-di-O-acetyl-5-deoxy-6-(dimethoxyphosphoryl)-L-gulonate | 1295541-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (6S)-5-acetamido-2,6-anhydro-3,4-di-O-acetyl-5-deoxy-6-(dimethoxyphosphoryl)-L-gulonate
• 英文别名: methyl (2S,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-dimethoxyphosphoryloxane-2-carboxylate
• CAS: 1295541-60-4
• 化学式: C₁₅H₂₄NO₁₁P
• 分子量: 425.329
• InChiKey: UBWNPEVGDWQCHZ-BIGJJFBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (6S)-5-acetamido-2,6-anhydro-3,4-di-O-acetyl-5-deoxy-6-(dimethoxyphosphoryl)-L-gulonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以0.21 g的产率得到methyl [(dimethylphosphonyl) 2-acetamido-1,2,4-trideoxy-3-O-acetyl-α-L-threo-hex-4-enopyranosid]uronate
  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：

  methyl [(dimethylphosphonyl) 2-acetamido-3,4-di-O-benzyl-1,2-dideoxy-β-D-glucopyranosid]uronate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 methyl (6S)-5-acetamido-2,6-anhydro-3,4-di-O-acetyl-5-deoxy-6-(dimethoxyphosphoryl)-L-gulonate
  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