(R)-[(4S,5S)-5-((R)-1-Hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxy-benzenesulfonylamino)-acetic acid methyl ester | 607707-80-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-[(4S,5S)-5-((R)-1-Hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxy-benzenesulfonylamino)-acetic acid methyl ester
• 英文别名: methyl (2R)-2-[(4S,5S)-5-[(1R)-1-hydroxy-2-methylsulfonyloxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4-methoxyphenyl)sulfonylamino]acetate
• CAS: 607707-80-2
• 化学式: C₁₈H₂₇NO₁₁S₂
• 分子量: 497.544
• InChiKey: XWGBORBAPTXQDJ-WCVJEAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (R)-[(4S,5S)-5-((R)-1-Hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxy-benzenesulfonylamino)-acetic acid methyl ester 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3aS,4R,7R,7aS)-7-hydroxy-5-(4'-methoxybenzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure–activity relationships of azasugar-based MMP/ADAM inhibitors

  摘要：

  In order to investigate structure-activity relationships of azasugar series toward metalloprotemases, we synthesized and evaluated several azasugar-based compounds. As a result, it was found that 4-phenoxybenzene derivative 3 having 2R,3R,4R,5S-configurations exhibited most potent inhibitory activities against matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00530-4
• 作为产物：
  描述：

  (R)-Azido-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 Muromac(R) (H⁺-form) 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-[(4S,5S)-5-((R)-1-Hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxy-benzenesulfonylamino)-acetic acid methyl ester
  参考文献：
  名称：

  Structure–activity relationships of azasugar-based MMP/ADAM inhibitors

  摘要：

  In order to investigate structure-activity relationships of azasugar series toward metalloprotemases, we synthesized and evaluated several azasugar-based compounds. As a result, it was found that 4-phenoxybenzene derivative 3 having 2R,3R,4R,5S-configurations exhibited most potent inhibitory activities against matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00530-4

文献信息

• US7223779B2
  申请人：——

  公开号：US7223779B2

  公开（公告）日：2007-05-29