(2S,5S,6S)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester | 924268-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,5S,6S)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S,6S)-2-(5-bromo-2-methoxy-3-phenylmethoxyphenyl)-3-methyl-3,6-dihydro-2H-pyran-6-carboxylate
• CAS: 924268-51-9
• 化学式: C₂₂H₂₃BrO₅
• 分子量: 447.326
• InChiKey: BSEMAIZDVIWIJD-DCPHZVHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S,6S)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester 在 三乙基硅烷 、 锂硼氢 、 Proton Sponge 、 dimethyl sulfide borane 、 4 A molecular sieve 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 45.5h， 生成 (2R,3S,5R)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol
  参考文献：
  名称：

  Mild Reductive Opening of Aryl Pyranosides Promoted by Scandium(III) Triflate

  摘要：

  DOI：

  10.1021/ja067234o
• 作为产物：
  描述：

  3-(benzyloxy)-5-bromo-2-methoxybenzaldehyde 、 methyl (2R,3S)-(E)-3-(dimethyl(phenyl)silyl)-2-(trimethylsilyloxy)-hex-4-enoate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(2S,5S,6S)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Reblastatin, Autolytimycin, and Non-Benzoquinone Analogues: Potent Inhibitors of Heat Shock Protein 90

  摘要：

  A full account of an asymmetric synthesis of reblastatin (1) and the first total synthesis of autolytimycin (2) and related structural compounds is described. The syntheses expand the utility of a highly regio- and diastereoselective hydrometalation aldehyde addition sequence to assemble the fully functionalized ansa chain of the natural products. Also documented is an intramolecular copper-mediated amidation reaction to close the 19-membered macrolactams. The amidation reaction was also employed for the generation of structural derivatives (6-9) of phenolic ansamycins. Ansamycin natural products and selected structural analogues were evaluated in a competitive binding assay to breast cancer cell lysate and a cytotoxicity assay. Both reblastatin (1) and autolytimycin (2) were shown to bind the heat shock protein 90 with enhanced binding activity (similar to 25 nM) than 17-allylamino-17-demethoxygeldanamycin (17-AAG, 4), a geldanamycin (3) derivative currently under evaluation for treatment of cancer (similar to 100 nM).

  DOI：

  10.1021/jo1000109