benzyl [(2R,5R)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate | 1052213-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl [(2R,5R)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate
• 英文别名: benzyl [(2S,5R)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate
• CAS: 1052213-45-2
• 化学式: C₃₃H₃₆N₂O₈
• 分子量: 588.657
• InChiKey: IAUJYZSQJRTLIU-LBNPDIFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  122.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl [(2R,5R)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate 在 ammonium cerium (IV) nitrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以70%的产率得到(S)-4-苄基-3-((R)-5-氧代四氢呋喃-3-羰基)恶唑烷-2-酮
  参考文献：
  名称：

  Stereoselective Formation of a Functionalized Dipeptide Isostere by Zinc Carbenoid-Mediated Chain Extension

  摘要：

  The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-extension reaction is demonstrated in the preparation of an amino acid-derived alpha-unsubstituted gamma-keto ester, which is incorporated into a framework that mimics a tetrapeptide. The identification of a suitable protecting group strategy facilitated the application of a tandem reaction for the incorporation of an alpha-side chain, and the use of an oxazolidinone auxiliary provided excellent diastereocontrol in a tandem chain-extension-aldol reaction. Stereoselectivity of the tandem chain-extension-aldol reaction was determined through application of a CAN-mediated oxidative cleavage reaction.

  DOI：

  10.1021/jo801993k
• 作为产物：
  描述：

  聚合甲醛 、 二碘甲烷 、 benzyl [(R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3,5-dioxopentan-2-yl](4-methoxybenzyl)carbamate 在 diethylzinc 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到benzyl [(2R,5R)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-(hydroxymethyl)-3,6-dioxohexan-2-yl](4-methoxybenzyl)carbamate
  参考文献：
  名称：

  Stereoselective Formation of a Functionalized Dipeptide Isostere by Zinc Carbenoid-Mediated Chain Extension

  摘要：

  The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-extension reaction is demonstrated in the preparation of an amino acid-derived alpha-unsubstituted gamma-keto ester, which is incorporated into a framework that mimics a tetrapeptide. The identification of a suitable protecting group strategy facilitated the application of a tandem reaction for the incorporation of an alpha-side chain, and the use of an oxazolidinone auxiliary provided excellent diastereocontrol in a tandem chain-extension-aldol reaction. Stereoselectivity of the tandem chain-extension-aldol reaction was determined through application of a CAN-mediated oxidative cleavage reaction.

  DOI：

  10.1021/jo801993k

文献信息

• Formation of γ-Lactones through CAN-Mediated Oxidative Cleavage of Hemiketals
  作者：Alexander M. Jacobine、Weimin Lin、Bethany Walls、Charles K. Zercher

  DOI：10.1021/jo801258h

  日期：2008.9.19

  The generation of substituted gamma-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an alpha-heteroatom. Formation of the gamma-lactone through the oxidative cleavage is used to assign stereochemistry of the

  取代的γ-内酯的产生可通过应用串联扩链​​-醛醇缩合反应，然后通过CAN介导的醛醇缩合产物的氧化裂解来完成。氧化裂解需要中间分子和α-杂原子的存在。通过氧化裂解形成γ-内酯可用于指定醛醇缩合反应的立体化学，并用作天然产物菜豆酸家族成员的短合成的最后一步。