(5S)-4-(benzyloxy)-1-methyl-5-{(1R)-1-[(triisopropylsilyl)oxy]ethyl}-1H-pyrrol-2(5H)-one | 1353654-76-8

• 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: (5S)-4-(benzyloxy)-1-methyl-5-{(1R)-1-[(triisopropylsilyl)oxy]ethyl}-1H-pyrrol-2(5H)-one
• 英文别名: (S)-4-(benzyloxy)-1-methyl-5-((R)-1-((triisopropylsilyl)oxy)ethyl)-1H-pyrrol-2(5H)-one；(2S)-1-methyl-3-phenylmethoxy-2-[(1R)-1-tri(propan-2-yl)silyloxyethyl]-2H-pyrrol-5-one
• CAS: 1353654-76-8
• 化学式: C₂₃H₃₇NO₃Si
• 分子量: 403.637
• InChiKey: VIZKGIOVIRJHJP-XXBNENTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-4-(benzyloxy)-1-methyl-5-{(1R)-1-[(triisopropylsilyl)oxy]ethyl}-1H-pyrrol-2(5H)-one 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 8.0h， 以93%的产率得到(5S)-5-{(1R)-1-[(triisopropylsilyl)oxy]ethyl}-1-methylpyrrolidine-2,4-dione
  参考文献：
  名称：

  青霉素C 1和双叠氮化物类似物的合成用于光亲和标记

  摘要：

  青霉代谢产物青霉素C 1的两种非对映异构体是通过将1-苏氨酸衍生的四酸与对映体纯的2-甲基辛基-（6 E）-烯酸进行3-酰化而首次合成的。5 S，6 R，9 S异构体的NMR光谱和旋光度与天然化合物相同。还合成了双叠氮化物标记的青霉素烯类似物，用于靶蛋白的光亲和标记。在甲醇（类似于蛋白质的亲核试剂）的存在下，双叠氮化物的光解仅导致芳基叠氮化物的反应，而苄基叠氮化物可用于下拉或附着荧光示踪剂。作为概念的证明，通过叠氮化物标签和膦荧光团之间的施陶丁格（Staudinger）连接，可以看到在活细胞中这种双叠氮化物标记的四酸的分布。

  DOI：

  10.1021/jo3026737
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl (4S)-4-[(1R)-1-acetyloxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate 在 哌啶 、 盐酸 、 三乙基硅烷 、 aluminum (III) chloride 、 caesium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 56.17h， 生成 (5S)-4-(benzyloxy)-1-methyl-5-{(1R)-1-[(triisopropylsilyl)oxy]ethyl}-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2

  摘要：

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.116

文献信息

• Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO
  作者：Inga Loke、Natja Park、Karl Kempf、Carsten Jagusch、Rainer Schobert、Sabine Laschat

  DOI：10.1016/j.tet.2011.10.099

  日期：2012.1

  alpha-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of beta-oxo functionalized alpha-aminoesters, e.g., esters of serine, threonine or beta-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the beta-OR group and on the configuration of beta-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2
  作者：Karl Kempf、Florian Schmitt、Ursula Bilitewski、Rainer Schobert

  DOI：10.1016/j.tet.2015.05.116

  日期：2015.8

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Penicillenol C₁ and of a Bis-Azide Analogue for Photoaffinity Labeling
  作者：Karl Kempf、Aruna Raja、Florenz Sasse、Rainer Schobert

  DOI：10.1021/jo3026737

  日期：2013.3.15

  enantiopure 2-methyloct-(6E)-enoic acids. The 5S,6R,9S isomer has NMR spectra and optical rotation identical with those of the natural compound. A bis-azide-tagged penicillenol analogue was also synthesized for photoaffinity labeling of target proteins. The photolysis of the bis-azide in the presence of methanol as a protein-mimicking nucleophile led to reaction only of the aryl azide, while leaving the

  青霉代谢产物青霉素C 1的两种非对映异构体是通过将1-苏氨酸衍生的四酸与对映体纯的2-甲基辛基-（6 E）-烯酸进行3-酰化而首次合成的。5 S，6 R，9 S异构体的NMR光谱和旋光度与天然化合物相同。还合成了双叠氮化物标记的青霉素烯类似物，用于靶蛋白的光亲和标记。在甲醇（类似于蛋白质的亲核试剂）的存在下，双叠氮化物的光解仅导致芳基叠氮化物的反应，而苄基叠氮化物可用于下拉或附着荧光示踪剂。作为概念的证明，通过叠氮化物标签和膦荧光团之间的施陶丁格（Staudinger）连接，可以看到在活细胞中这种双叠氮化物标记的四酸的分布。