(3aR,6R,6aS)-6-benzyloxymethyl-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester | 1055312-47-4

• 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: (3aR,6R,6aS)-6-benzyloxymethyl-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester
• 英文别名: methyl (3aR,6R,6aS)-6-(benzyloxymethyl)-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydro-2H-furo[2,3-c]pyrrole-6-carboxylate；methyl (3aR,6R,6aS)-5-[(4-methoxyphenyl)methyl]-6a-methyl-2,4-dioxo-6-(phenylmethoxymethyl)-3,3a-dihydrofuro[2,3-c]pyrrole-6-carboxylate
• CAS: 1055312-47-4
• 化学式: C₂₅H₂₇NO₇
• 分子量: 453.492
• InChiKey: OCWNTPGBLJQWHI-OPXMRZJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,6R,6aS)-6-benzyloxymethyl-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以84%的产率得到(3aR,6R,6aS)-6-hydroxymethyl-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization–lactonization as a key step

  摘要：

  Application of a sequential nickel-catalyzed reductive aldol cyclization-lactonization reaction in a short formal synthesis of salinsporamide A, a potent 20S proteasome inhibitor and anti-cancer compound, is described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.038
• 作为产物：
  描述：

  (R)-ethyl (E)-3-[N-(1-benzyloxymethyl-1-carbomethoxy-2-oxopropyl)-N-(4-methoxybenzyl)carbamoyl]acrylate 在 (Me₃P)2NiCl₂ diethylzinc 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以42%的产率得到(3aR,6R,6aS)-6-benzyloxymethyl-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization–lactonization as a key step

  摘要：

  Application of a sequential nickel-catalyzed reductive aldol cyclization-lactonization reaction in a short formal synthesis of salinsporamide A, a potent 20S proteasome inhibitor and anti-cancer compound, is described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.038

文献信息

• Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization
  作者：Justin R. Struble、Jeffrey W. Bode

  DOI：10.1016/j.tet.2009.03.103

  日期：2009.6

  carbene (NHC) catalyzed intramolecular lactonization to prepare densely functionalized bicyclic γ-lactam-γ-lactone adducts from enals is reported. This method has been applied to the formal synthesis of salinosporamide A, a potent 20S proteasome inhibitor and anti-cancer therapeutic.

  报道了N-杂环卡宾 (NHC) 催化分子内内酯化以从 enals 制备密集功能化的双环 γ-内酰胺-γ-内酯加合物。该方法已应用于盐孢菌素 A 的正式合成，这是一种有效的 20S 蛋白酶体抑制剂和抗癌治疗剂。
• Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization–lactonization as a key step
  作者：Isabel Villanueva Margalef、Leszek Rupnicki、Hon Wai Lam

  DOI：10.1016/j.tet.2008.06.038

  日期：2008.8

  Application of a sequential nickel-catalyzed reductive aldol cyclization-lactonization reaction in a short formal synthesis of salinsporamide A, a potent 20S proteasome inhibitor and anti-cancer compound, is described. (C) 2008 Elsevier Ltd. All rights reserved.