(1"S,2R,4'R,5'R)-[5'-(1"-hydroxy-2"-methanesulfonyloxy-ethyl)-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-(4-phenoxybenzenesulfonylamino)-acetic acid methyl ester | 607707-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1"S,2R,4'R,5'R)-[5'-(1"-hydroxy-2"-methanesulfonyloxy-ethyl)-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-(4-phenoxybenzenesulfonylamino)-acetic acid methyl ester
• 英文别名: methyl (2R)-2-[(4R,5R)-5-[(1S)-1-hydroxy-2-methylsulfonyloxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4-phenoxyphenyl)sulfonylamino]acetate
• CAS: 607707-94-8
• 化学式: C₂₃H₂₉NO₁₁S₂
• 分子量: 559.615
• InChiKey: IVRGSMGHIXUDAV-DOIPELPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (1"S,2R,4'R,5'R)-[5'-(1"-hydroxy-2"-methanesulfonyloxy-ethyl)-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-(4-phenoxybenzenesulfonylamino)-acetic acid methyl ester 在 sodium hydroxide 、 Muromac(R) (H⁺-form) 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4R,5S)-3,4,5-trihydroxy-1-(4'-phenoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide
  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：

  Methyl 2-azido-2-deoxy-3,4:5,6-O-diisopropylidene-L-idonate 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 (1"S,2R,4'R,5'R)-[5'-(1"-hydroxy-2"-methanesulfonyloxy-ethyl)-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-(4-phenoxybenzenesulfonylamino)-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

• EP1516872
  申请人：——

  公开号：——

  公开（公告）日：——
• US7223779B2
  申请人：——

  公开号：US7223779B2

  公开（公告）日：2007-05-29