γ-Benzyl (2S)-2-hydroxyglutaric acid | 156693-50-4

• 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: γ-Benzyl (2S)-2-hydroxyglutaric acid
• 英文别名: (S)-5-(benzyloxy)-2-hydroxy-5-oxopentanoic acid；γ-benzyl 2-hydroxy-glutaric acid；5-benzyloxycarbonyl-2-hydroxy-pentanedioic acid；(2S)-2-hydroxy-5-oxo-5-benzyloxypentanoic acid；(S)-2-Hydroxy-pentanedioic Acid 5-(Phenylmethyl) Ester；(2S)-2-hydroxy-5-oxo-5-phenylmethoxypentanoic acid
• CAS: 156693-50-4
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: OCPVHWNYJXUPHN-JTQLQIEISA-N

物化性质

• 沸点：
  454.5±40.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  γ-Benzyl (2S)-2-hydroxyglutaric acid 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 、 碳酸氢钠 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， -60.0~30.0 ℃ 、344.73 kPa 条件下， 反应 74.0h， 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：

  苯甲醇 在 甲烷磺酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 甲苯 为溶剂， 反应 9.0h， 生成 γ-Benzyl (2S)-2-hydroxyglutaric acid
  参考文献：
  名称：

  Organo-Catalyzed Ring Opening Polymerization of a 1,4-Dioxane-2,5-dione Deriving from Glutamic Acid

  摘要：

  The (3S)-[(benzyloxycarbonypethyl)-1,4-dioxan-2,5-dione (BED) was prepared in four steps starting from glutamic acid and bromoacetyl bromide. According to X-ray diffraction analysis, the pendant functional group is located in equatorial position and points away from the six-membered ring. The organo-catalyzed ring-opening polymerization of BED was promoted with 4-dimethylaminopyridine (DMAP) and the combination of thiourea TUCy and (-)-sparteine. PolyBED samples of number-average molar mass M-n up to 36000 and narrow polydispersity (M-w/M-n < 1.25) were thereby prepared in a controlled manner under mild conditions (dichloromethane solution, 30 degrees C), as substantiated by size-exclusion chromatography, matrix-assisted laser desorption ionization time-of-flight-mass spectrometry (MALDI-TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy. The pendant functional group does not interfere with the polymerization and BED was even found to be slightly more reactive than lactide. Despite the strongly dissymmetric substitution pattern of the 1,4-dioxan-2,5-dione core, the ensuing polyBED polymers present a random distribution of glycolic-[(benzyloxycarbonyl)ethyl]glycolic (gly glu) units, as supported by a H-1-C-13 HMBC 2D NMR experiment. The preparation of 1:1 adducts with n-pentanol confirmed that ring-opening of BED occurs almost indifferently on either of the endocyclic ester groups. Poly(alpha-hydroxyacids) featuring pendant carboxylic acids were finally obtained by acetylation of the terminal OH groups followed by hydrogenolysis.

  DOI：

  10.1021/bm100433c

文献信息

• Functionalized polyesters from organocatalyzed ROP of gluOCA, the O-carboxyanhydride derived from glutamic acid
  作者：Olivier Thillaye du Boullay、Colin Bonduelle、Blanca Martin-Vaca、Didier Bourissou

  DOI：10.1039/b800852c

  日期：——

  Well-controlled poly(α-hydroxyacids) featuring pendant carboxylic acid groups were prepared under mild conditions viaDMAP-catalyzed ROP of the O-carboxyanhydrides derived from glutamic and lactic acids.

  在温和条件下，通过DMAP催化的O-羧酸酐的ROP反应，制备了带有侧链羧酸基团的良好控制的聚（α-羟基酸）。这些O-羧酸酐来源于谷氨酸和乳酸。
• HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP3018126A1

  公开（公告）日：2016-05-11

  The present invention relates to compound (I) or a salt thereof which has a RORγt inhibitory action. wherein each symbol is as defined in the specification.

  本发明涉及具有 RORγt 抑制作用的化合物 (I) 或其盐。 其中各符号如说明书中所定义。
• Heterocyclic compound
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US10053468B2

  公开（公告）日：2018-08-21

  The present invention relates to compound (I) or a salt thereof which has a RORγt inhibitory action. wherein each symbol is as defined in the specification.

  本发明涉及具有 RORγt 抑制作用的化合物 (I) 或其盐。 其中各符号如说明书中所定义。
• 一种20-羟基黄体酮前体化合物及其制备方法和应用
  申请人：新疆医科大学

  公开号：CN115960154A

  公开（公告）日：2023-04-14

  本发明提供了一种20‑羟基黄体酮前体化合物及其制备方法和应用，属于药物制备技术领域。本发明提供了一种20‑羟基黄体酮前体化合物，将黄体酮衍生物20‑羟基黄体酮通过不同的连接桥与甘油三酯骨架相连，合成不同结构的20‑羟基黄体酮甘油三酯前药，该类前药经胃肠道可模拟甘油三酯在肠道中的特异性消化过程，趋向淋巴转运，避开肝首过效应，从而提高母药20‑羟基黄体酮的口服生物利用度，且不同结构的连接桥将影响前药的体内过程，从而影响口服生物利用度。
• TW2016/2105
  申请人：——

  公开号：——

  公开（公告）日：——