(3aR,6R,6aS)-6-[(S)-{(S)-cyclohex-2-enyl}hydroxymethyl]-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester | 1055312-51-0

• 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-[(S)-{(S)-cyclohex-2-enyl}hydroxymethyl]-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-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-5-[(4-methoxyphenyl)methyl]-6a-methyl-2,4-dioxo-3,3a-dihydrofuro[2,3-c]pyrrole-6-carboxylate
• CAS: 1055312-51-0
• 化学式: C₂₄H₂₉NO₇
• 分子量: 443.497
• InChiKey: KDDXJUPXSSNRLP-YJYRJYHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,6R,6aS)-6-[(S)-{(S)-cyclohex-2-enyl}hydroxymethyl]-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以60%的产率得到(2R,3S,4R)-2-[(S)-{(S)-cyclohex-2-enyl}hydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl)-1-(4-methoxybenzyl)-3-methyl-5-oxopyrrolidine-2-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：

  (3aR,6R,6aS)-6-formyl-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester 、 tributyl(cyclohex-2-en-1-yl)stannane 在 正丁基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以22.4 g的产率得到(3aR,6R,6aS)-6-[(S)-{(S)-cyclohex-2-enyl}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

文献信息

• 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.