(S)-1,5-bis(benzyloxy)-2-(2,3-dihydroxy-2-methylpropyl)anthracene-9,10-dione | 1349697-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (S)-1,5-bis(benzyloxy)-2-(2,3-dihydroxy-2-methylpropyl)anthracene-9,10-dione
• 英文别名: (S)-1,5-bis(benzyloxy)-2-(2-methylallyl)anthracene-9,10-dione
• CAS: 1349697-73-9
• 化学式: C₃₂H₂₈O₆
• 分子量: 508.571
• InChiKey: GQMPHCDRNAYYTQ-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-1,5-bis(benzyloxy)-2-(2,3-dihydroxy-2-methylpropyl)anthracene-9,10-dione 在 1,4-环己二烯 、 palladium 10% on activated carbon 、 bis(tetrahydrofuran)-meso-tetra(4-chlorophenyl)porphyrinato aluminum tetracarbonyl cobaltate 、 水 、 sodium hydride 、 二正丁基氧化锡 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 mineral oil 为溶剂， 40.0 ℃ 、6.21 MPa 条件下， 反应 23.0h， 生成 (S)-4-(1,5-dihydroxy-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
• 作为产物：
  描述：

  溴甲苯 在 四氧化锇 、 hydroquinidine 1 4-phthalazinediyl diether 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 生成 (S)-1,5-bis(benzyloxy)-2-(2,3-dihydroxy-2-methylpropyl)anthracene-9,10-dione
  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

• Convergent de novo synthesis of vineomycinone B2 methyl ester
  作者：Qian Chen、Yashan Zhong、George A. O'Doherty

  DOI：10.1039/c3cc44050h

  日期：——

  An efficient de novo synthesis of vineomycinone B2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available starting materials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, which were joined by a convergent late stage Suzuki's glycosylation for the construction of the aryl beta-C-glycoside

  已经实现了葡萄霉素 B2 甲酯的有效从头合成。最长的线性路线仅需要从非手性市售起始材料（总产率为 4.0%）的 14 个步骤。关键转化包括两个关键片段的从头不对称合成，这些片段通过收敛的后期 Suzuki 糖基化加入，用于构建芳基 β-C-糖苷。随后的 BBr3 一锅脱苄基、去甲基化和空气氧化提供了葡萄霉素 B2 甲酯。