(R)-(-)-γ-benzyloxymethyl-γ-butyrolactone | 77697-15-5

• 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: (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone
• 英文别名: (R)-5-(benzyloxymethyl)tetrahydro-2-furanone；(R)-5-benzyloxymethyl-γ-butyrolactone；5-Benzyloxymethyldihydrofuran-2-one；(R)-4-benzyloxymethyl-4-butanolide；5-benzyloxypentane-4-olide；(R)-5-Benzyloxymethyl-dihydro-furan-2-one；(5R)-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 77697-15-5
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: JVPPZBQIEINDEG-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone 在 palladium dihydroxide 吡啶 、 盐酸 、 三甲基氯硅烷 、 三乙基硼 、 三正丁基氢锡 、 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 环己烯 为溶剂， 反应 2.0h， 生成 (-)-ethyl 4-[(2S,5R)-(5-hydroxymethyl)tetrahydrofuran-2-yl]imidazole-1-carboxylate
  参考文献：
  名称：

  Synthesis of imifuramine and its stereoisomers exhibiting histamine H3-agonistic activity

  摘要：

  The four possible stereoisomers of a novel imidazole C-nucleoside derivative were synthesized by the efficient use of a PhSe group. Among them, (+)-4(5)-[(2R,5R)-5-(aminomethyl)tetrahydrofuran-2-yl]imidazole (imifuramine) was indicated as a novel type of histamine H-3-agonist by a brain microdialysis method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00202-6
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 magnesium chloride 作用下， 以 various solvent(s) 为溶剂， 反应 9.0h， 生成 (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone
  参考文献：
  名称：

  Takano, Seiichi; Goto, Emiko; Hirama, Michiyasu, Heterocycles, 1981, vol. 16, # 3, p. 381 - 385

  摘要：

  DOI：

文献信息

• Novel Chiral Glycerol Analogues Building Blocks. Application to the Synthesis of Bioactive Glycoglycerolipid Analogues
  作者：Patrizia Ferraboschi、Diego Colombo、Federica Compostella、Shahrzad Reza-Elahi

  DOI：10.1055/s-2001-16789

  日期：——

  Monoacylglycosylglycerols show anti-tumor promoting effects: in order to study the role of the ester function we have prepared by simple methods (R)-1-O-benzyl-1,2-decandiolk (R)-3-O-benzyl-1-O-hexyl-su-glycerol, and (R)-1-O-benzyl-5-oxo-1,2-decandiol; these optically active compounds are building blocks for the synthesis of monohexanoylglycosylglycerol isosters.

  单酰基糖苷甘油显示出抗肿瘤促进作用：为了研究酯基的作用，我们通过简单的方法合成了 (R)-1-O-苄基-1,2-癸二醇、(R)-3-O-苄基-1-O-己基-甘油和 (R)-1-O-苄基-5-氧-1,2-癸二醇；这些光学活性化合物是合成单己酰基糖苷甘油同分异构体的构建块。
• Drug Delivery by an Enzyme-Mediated Cyclization of a Lipid Prodrug with Unique Bilayer-Formation Properties
  作者：Lars Linderoth、Günther H. Peters、Robert Madsen、Thomas L. Andresen

  DOI：10.1002/anie.200805241

  日期：2009.2.23

  Special delivery: Liposomal drug‐delivery systems in which prodrugs are activated specifically by disease‐associated enzymes have great potential for the treatment of severe diseases, such as cancer. A new type of phospholipid‐based prodrug has the ability to form stable small unilamellar vesicles (see picture). Activation of the prodrug vesicles by the enzyme sPLA2 initiates a cyclization reaction

  特殊递送：脂质体药物递送系统中的前药被疾病相关的酶特异性激活，在治疗严重疾病（如癌症）方面具有巨大潜力。一种新型的磷脂基前药具有形成稳定的单层小囊泡的能力（见图）。sPLA 2酶激活前药囊泡会引发环化反应，从而导致药物释放。
• Svetamycins A–G, Unusual Piperazic Acid-Containing Peptides from <i>Streptomyces</i> sp.
  作者：Denis Dardić、Gianluigi Lauro、Giuseppe Bifulco、Patricia Laboudie、Peyman Sakhaii、Armin Bauer、Andreas Vilcinskas、Peter E. Hammann、Alberto Plaza

  DOI：10.1021/acs.joc.7b00228

  日期：2017.6.16

  amino acids including a rare 4,5-dihydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylic acid, a γ-halogenated piperazic acid, and a novel δ-methylated piperazic acid in svetamycins B–C, E, and G. Moreover, isotope-labeled substrate feeding experiments demonstrated ornithine as the precursor of piperazic acid and that methylation at the δ position of the piperazyl scaffold is S-adenosyl-l-methionine (SAM)-dependent

  七个新卤代肽称为svetAMycins A-G（1 - 7）从一个实验室培养物已被分离链霉菌sp。SvetAMycins A–D，F和G是环短肽，而SvetAMycin E是SvetAMycin C的线性类似物。其结构是通过广泛的光谱分析确定的，其立体化学构型是通过NMR数据，量子力学计算，和化学衍生化。SvetAMycins的特征是存在羟基乙酸和五个氨基酸，包括稀有的4,5-二羟基-2,3,4,5-四氢哒嗪-3-羧酸，γ-卤代哌嗪酸和新的δ在svetAMycins B-C，E，和G甲基化的六氢哒嗪酸此外，同位素标记的底物馈送实验证明鸟氨酸作为六氢哒嗪酸的前体和甲基化在哌嗪骨架的δ位置是小号-adenosyl-升-蛋氨酸（SAM）依赖。SvetAMycin G是这套化合物中最有效的抗菌剂，其MIC 80值为2μg/ mL ，可抑制耻垢分枝杆菌的生长。
• Synthesis of Clavulones (Claviridenones) via [3+2] Annulation Using Reaction of (β-(Phenylthio)acryloyl)silane with Lithium Enolate of Alkyl Methyl Ketone
  作者：Kei Takeda、Akemi Nakajima、Eiichi Yoshii

  DOI：10.1055/s-1997-781

  日期：1997.3

  Synthesis of clavulones II (1) and III (2) (claviridenones c and b), antitumor marine prostanoids, has been achieved via [3+2] annulation using reaction of (β-(phenylthio)acryloyl)silane 5 with methyl ketone enolate 6 followed by installation of the α-side chain by aldol reaction.

  克拉维酮 II (1) 和 III (2)（claviridenones c 和 b）、抗肿瘤海洋前列腺素类化合物的合成，已通过 (β-(苯硫基)丙烯酰基)硅烷 5 与甲基酮烯醇化物的反应通过 [3+2] 成环实现。 6 随后通过羟醛反应安装α-侧链。
• Condensation of a Chiral Tetrahydro-2-furanthione with Diazocarbonyl Compounds
  作者：Seiichi Takano、Shun'ichi Tomita、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1055/s-1987-28190

  日期：——

  Reaction of (R)-5-(benzyloxymethyl)tetrahydro-2-furanthione (2), prepared from the corresponding furanone 1, with the diazocarbonyl compounds 3a-c in the presence of rhodium(II) acetate afforded the 2-(acylmethylene)tetrahydrofuran derivatives 4a-c in good yields.

  在乙酸铑（II）存在下，由相应的呋喃酮 1 制备的 (R)-5-(benzyloxymethyl)tetrahydro-2-furanthione (2)与重氮羰基化合物 3a-c 反应，得到 2-(酰亚甲基)四氢呋喃衍生物 4a-c，产率良好。