(R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid | 1349697-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid
• 英文别名: (3R)-4-[9,10-dioxo-1,5-bis(phenylmethoxy)anthracen-2-yl]-3-hydroxy-3-methylbutanoic acid
• CAS: 1349697-72-8
• 化学式: C₃₃H₂₈O₇
• 分子量: 536.581
• InChiKey: VUHKMGDFQICEBX-MGBGTMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid 在 1,4-环己二烯 、 palladium 10% on activated carbon 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以88%的产率得到(R)-(+)-Fridamycin E
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Fridamycin E

  摘要：

  A de novo asymmetric synthesis of (R)- and (S)-fridamycin E has been achieved. The entirely linear route required only nine steps from commercially available starting materials (16% overall yield). Key transformations included a Claisen rearrangement, a Sharpless dihydroxylation and a cobalt-catalyzed epoxide carbonylation to give a beta-lactone intermediate. Antibacterial activities were determined for both enantiomers using two strains of E. coli, with the natural (R)-enantiomer showing significant inhibition against a Gram-(+)-like imp strain (MIC = 8 mu M).

  DOI：

  10.1021/ol203041b
• 作为产物：
  描述：

  (R)-1,5-bis(benzyloxy)-2-((2-methyl-4-oxooxetan-2-yl)methyl)anthracene-9,10-dione 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到(R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Fridamycin E

  摘要：

  A de novo asymmetric synthesis of (R)- and (S)-fridamycin E has been achieved. The entirely linear route required only nine steps from commercially available starting materials (16% overall yield). Key transformations included a Claisen rearrangement, a Sharpless dihydroxylation and a cobalt-catalyzed epoxide carbonylation to give a beta-lactone intermediate. Antibacterial activities were determined for both enantiomers using two strains of E. coli, with the natural (R)-enantiomer showing significant inhibition against a Gram-(+)-like imp strain (MIC = 8 mu M).

  DOI：

  10.1021/ol203041b

文献信息

• <i>De Novo</i> Asymmetric Synthesis of Fridamycin E
  作者：Qian Chen、Michael Mulzer、Pei Shi、Penny J. Beuning、Geoffrey W. Coates、George A. O’Doherty

  DOI：10.1021/ol203041b

  日期：2011.12.16

  A de novo asymmetric synthesis of (R)- and (S)-fridamycin E has been achieved. The entirely linear route required only nine steps from commercially available starting materials (16% overall yield). Key transformations included a Claisen rearrangement, a Sharpless dihydroxylation and a cobalt-catalyzed epoxide carbonylation to give a beta-lactone intermediate. Antibacterial activities were determined for both enantiomers using two strains of E. coli, with the natural (R)-enantiomer showing significant inhibition against a Gram-(+)-like imp strain (MIC = 8 mu M).