5-Benzyl 1-methyl 2-hydroxyglutarate | 156693-51-5

• 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: 5-Benzyl 1-methyl 2-hydroxyglutarate
• 英文别名: (S)-5-benzyl 1-methyl 2-hydroxypentanedioate；5-O-benzyl 1-O-methyl (2S)-2-hydroxypentanedioate
• CAS: 156693-51-5
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: SRRBWVPUZXZPRC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Benzyl 1-methyl 2-hydroxyglutarate 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -60.0~30.0 ℃ 、344.73 kPa 条件下， 反应 26.0h， 生成 Methyl (2S)-2-(benzoyloxy)-5-oxopentanoate
  参考文献：
  名称：

  Synthesis of the Enantiomeric Furobenzofurans, Late Precursors for the Synthesis of (+)- and (-)-Aflatoxins B1, B2, G1, and G2

  摘要：

  Enantiomeric tetrahydrofuro[2,3-b]benzofurans, representing the ABC tricyclic portion of aflatoxins B-1, B-2, G(1), and G(2), were generated from the oxaza-Cope rearrangement of a suitably functionalized O-aryloxime. The O-aryloxime was, in turn, made from the condensation of an enantiomerically pure aldehyde derived from glutamic acid and a substituted phenoxyamine. High regioselectivity with respect to the A-ring substituents of the ABC tricycle was achieved through the use of electrochemistry. The regioselective electrochemical cleavage of 4,6-bis(tosyloxy)-2-(methoxycarbonyl)-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran (22) resulted in a 97/3 mixture of regioisomeric phenols. The regiochemical assignments of the resulting phenols were determined by 2D NOESY NMR. The enantiomeric ratio of the final product was determined to be 96/4 by NMR analysis of diastereomers resulting from the coupling of 31a to (+)- and (+/-)-phenethylamine.

  DOI：

  10.1021/jo00093a008
• 作为产物：
  描述：

  L-谷氨酸 在 硫酸 、 水 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醚 为溶剂， 反应 7.0h， 生成 5-Benzyl 1-methyl 2-hydroxyglutarate
  参考文献：
  名称：

  来自 Ambrostoma quadriimpressum Motschulsky 的新苯乙基烷基酰胺。

  摘要：

  从甲虫 Ambrostoma quadriimpressum Motschulsky 中分离出一种新的苯乙基烷基酰胺 (10R)-10-羟基-N-苯乙基十八酰胺 (1)。酰胺的结构由NMR和MS确定。化合物 1 的绝对构型通过不对称全合成得到证实，该合成从 L-谷氨酸开始。脂肪链的构建是通过羟基的选择性保护和 Wittig 烯化反应的两次实施来完成的。

  DOI：

  10.3762/bjoc.7.158

文献信息

• BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine
  作者：Ru-Cheng Liu、Wei Huang、Jing-Yi Ma、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1016/j.tetlet.2009.04.097

  日期：2009.7

  The asymmetric BF3 center dot Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based on this nucleophilic substitution. In addition, N,O-acetal 10 was synthesized from L-benzyl glutamate in 11 steps. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of febrifuginol analogues and evaluation of their biological activities
  作者：Huong Doan Thi Mai、Giang Vo Thanh、Van Hieu Tran、Van Nam Vu、Van Loi Vu、Bich Ngan Truong、Thi Dao Phi、Van Minh Chau、Van Cuong Pham

  DOI：10.1016/j.tetlet.2014.11.028

  日期：2014.12

  A new series of febrifuginol analogues was prepared from L-glutamic acid. An antimalarial activity evaluation against chloroquine-sensitive (T96) and chloroquine-resistant (K1) Plasmodium falciparum indicated that all the tested compounds had very strong inhibitory activity. Compounds 4 and 17b' were inactive against KB, MCF7, HepG2 and LU1 cell lines even at a concentration of 100 mu M, while they exhibited significant inhibition towards P. falciparum. Comparison of the antimalarial activity and the cytotoxic properties revealed that the 2'S isomers were more active than the corresponding 2'R isomers for this series of febrifuginol analogues, indicating that the C-2' position is critical for the biological activity of this class of compounds. (C) 2014 Elsevier Ltd. All rights reserved.
• A new phenylethyl alkyl amide from the <i>Ambrostoma quadriimpressum</i> Motschulsky
  作者：Guolei Zhao、Chao Yang、Bing Li、Wujiong Xia

  DOI：10.3762/bjoc.7.158

  日期：——

  isolated from the beetle Ambrostoma quadriimpressum Motschulsky. The structure of the amide was determined by NMR and MS. The absolute configuration of compound 1 was confirmed by an asymmetric total synthesis, which was started from L-glutamic acid. The construction of the aliphatic chain was accomplished by the selective protection of the hydroxy groups and two-time implementation of the Wittig olefination

  从甲虫 Ambrostoma quadriimpressum Motschulsky 中分离出一种新的苯乙基烷基酰胺 (10R)-10-羟基-N-苯乙基十八酰胺 (1)。酰胺的结构由NMR和MS确定。化合物 1 的绝对构型通过不对称全合成得到证实，该合成从 L-谷氨酸开始。脂肪链的构建是通过羟基的选择性保护和 Wittig 烯化反应的两次实施来完成的。
• Synthesis of the Enantiomeric Furobenzofurans, Late Precursors for the Synthesis of (+)- and (-)-Aflatoxins B1, B2, G1, and G2
  作者：Edgar R. Civitello、Henry Rapoport

  DOI：10.1021/jo00093a008

  日期：1994.7

  Enantiomeric tetrahydrofuro[2,3-b]benzofurans, representing the ABC tricyclic portion of aflatoxins B-1, B-2, G(1), and G(2), were generated from the oxaza-Cope rearrangement of a suitably functionalized O-aryloxime. The O-aryloxime was, in turn, made from the condensation of an enantiomerically pure aldehyde derived from glutamic acid and a substituted phenoxyamine. High regioselectivity with respect to the A-ring substituents of the ABC tricycle was achieved through the use of electrochemistry. The regioselective electrochemical cleavage of 4,6-bis(tosyloxy)-2-(methoxycarbonyl)-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran (22) resulted in a 97/3 mixture of regioisomeric phenols. The regiochemical assignments of the resulting phenols were determined by 2D NOESY NMR. The enantiomeric ratio of the final product was determined to be 96/4 by NMR analysis of diastereomers resulting from the coupling of 31a to (+)- and (+/-)-phenethylamine.