(S)-5-<(benzyloxy)methyl>-5-(hydroxymethyl)tetrahydro-2-furanone | 173256-42-3

• 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: (S)-5-<(benzyloxy)methyl>-5-(hydroxymethyl)tetrahydro-2-furanone
• 英文别名: (R)-5-(hydroxymethyl)-5-[(phenylmethoxy)methyl]-3,4,5-trihydrofuran-2-one；(S)-5-[(Benzyloxy)methyl]-5-(hydroxymethyl)-tetrahydro-2-furanone；(5S)-5-(hydroxymethyl)-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 173256-42-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: OBIWUMHFPMQLMA-ZDUSSCGKSA-N

物化性质

• 沸点：
  412.2±15.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-<(benzyloxy)methyl>-5-(hydroxymethyl)tetrahydro-2-furanone 在 钯 吡啶 、 咪唑 、 甲酸 、 二异丁基氢化铝 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 53.0h， 生成 {2-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-5-methoxyoxolan-2-yl}methyl acetate
  参考文献：
  名称：

  The triphosphate of β-d-4′-C-ethynyl-2′,3′-dideoxycytidine is the preferred enantiomer substrate for HIV reverse transcriptase

  摘要：

  The enantioselective synthesis of the beta-D (1) enantiomer of 4-C-ethynyl-2',3'-dideoxycytidine confirms an earlier stereochemical assignment that was strictly based on the ability of HIV reverse transcriptase and its M184V mutant to discriminate between the D- and L-configuration of nucleoside 5'-triphosphates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.061
• 作为产物：
  描述：

  (R)-5-[(phenylmethoxy)methyl]-5-[(triphenylmethoxy)methyl]-4,5-dihydrofuran-2(3H)-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88.9%的产率得到(S)-5-<(benzyloxy)methyl>-5-(hydroxymethyl)tetrahydro-2-furanone
  参考文献：
  名称：

  The triphosphate of β-d-4′-C-ethynyl-2′,3′-dideoxycytidine is the preferred enantiomer substrate for HIV reverse transcriptase

  摘要：

  The enantioselective synthesis of the beta-D (1) enantiomer of 4-C-ethynyl-2',3'-dideoxycytidine confirms an earlier stereochemical assignment that was strictly based on the ability of HIV reverse transcriptase and its M184V mutant to discriminate between the D- and L-configuration of nucleoside 5'-triphosphates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.061

文献信息

• DIACYLGLYCEROL LACTONE COMPOUND, PREPARATION METHOD THEREFOR, AND IMMUNOSTIMULATOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：ENZYCHEM LIFESCIENCES CORPORATION

  公开号：US20210002242A1

  公开（公告）日：2021-01-07

  Disclosed are a novel diacylglycerol lactone compound for improving immunity and inhibiting infection by promoting neutrophil movement, a preparation method therefor, and an immunostimulator containing same as an active ingredient. The diacyloglycerol lactone compound is represented by chemical formula 1 of the specification. In chemical formula 1, R1 and R2 are respectively N and independently a C2-30 fatty acid group.

  本发明揭示了一种新颖的二酰甘油内酯化合物，用于通过促进中性粒细胞运动来提高免疫力和抑制感染，以及其制备方法和包含该化合物作为活性成分的免疫刺激剂。该二酰甘油内酯化合物由规范中的化学式1表示。在化学式1中，R1和R2分别为N和独立的C2-30脂肪酸基团。
• Conformationally constrained diacylglycerol analogues
  申请人：The United States of America as represented by the Department of Health

  公开号：US05874464A1

  公开（公告）日：1999-02-23

  Conformationally constrained diacylglycerol analogues, pharmaceutical compositions comprising such analogues, and methods of using such analogues as agonists and antagonists of protein kinase C.

  构象限制的二酰基甘油类似物、包含这种类似物的制药组合物，以及使用这种类似物作为蛋白激酶C的激动剂和拮抗剂的方法。
• Conformationally Constrained Analogues of Diacylglycerol. 11. Ultrapotent Protein Kinase C Ligands Based on a Chiral 5-Disubstituted Tetrahydro-2-furanone Template
  作者：Jeewoo Lee、Shaomeng Wang、George W. A. Milne、Rajiv Sharma、Nancy E. Lewin、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm950277n

  日期：1996.1.1

  of PK-C with DAG is stereospecific, it was anticipated that PK-C would bind tightly to only one enantiomeric form of the compounds constructed with this new lactone template. Separation of enantiomers by chiral HPLC was discarded due to the ease with which acyl migration occurs in these class of compounds, and a total chiral synthesis was undertaken. Prior to chemical synthesis, the selection of the

  以前显示在外消旋5（-）[（（酰氧基）-甲基] -5-（羟甲基）四氢-2-呋喃酮）模板上构象受限的二酰基甘油（DAG）类似物具有出色的结合蛋白激酶C（PK- C）。由于PK-C与DAG的相互作用是立体特异性的，因此可以预期，PK-C仅与该新内酯模板构建的化合物的仅一种对映体形式紧密结合。由于在这类化合物中容易发生酰基迁移，因此放弃了通过手性HPLC分离对映体的方法，并进行了总的手性合成。在化学合成之前，通过分子构象分析预测了“正确的”对映体模板的选择，该构象分析将DAG的两种对映体的假定“活性”进行了比较。两个对映体内酯模板的构象。DAG的这种“活性”构象源自先前开发的药效团模型，该模型使用强力佛波二酯分子作为理想的刚性模板。该分析的结果表明“正确的”内酯模板对应于DAG的非活性（R）-异构体。该分析还预测对应于活性（S）-DAG对映异构体的内酯模板不能充分地适合药效基团。从共同的双环中间体（5R，8R，9R）-8
• Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones
  作者：Anne Paju、Marit Laos、Artur Jõgi、Malle Päri、Raissa Jäälaid、Tõnis Pehk、Tõnis Kanger、Margus Lopp

  DOI：10.1016/j.tetlet.2006.04.013

  日期：2006.6

  3-Alkyl-1,2-cyclopentanediones 1 are transformed into 2-alkyl-2-hydroxyglutaric acid gamma-lactones 3 in up to 83% isolated yields and up to 96% ee, affording a simple access to many bioactive compounds, including diacylglycerol lactones (DAG-lactones). (c) 2006 Elsevier Ltd. All rights reserved.
• US5874464A
  申请人：——

  公开号：US5874464A

  公开（公告）日：1999-02-23