(S)-5-(benzoyloxymethyl)tetrahydrofuran-2-one | 32780-07-7

• 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-(benzoyloxymethyl)tetrahydrofuran-2-one
• 英文别名: [(2S)-5-Oxotetrahydro-2-furanyl]methyl benzoate；[(2S)-5-oxooxolan-2-yl]methyl benzoate
• CAS: 32780-07-7
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: HZLYSMGNNYHFQU-JTQLQIEISA-N

物化性质

• 熔点：
  60.0-60.5 °C
• 沸点：
  388.3±15.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-(benzoyloxymethyl)tetrahydrofuran-2-one 在 adenosine deaminase 氨 、 水 作用下， 以 甲醇 为溶剂， 生成 2',3'-二脱氧肌苷
  参考文献：
  名称：

  2'，3'-双脱氧核苷的新合成方法可用于辅助化疗

  摘要：

  由L-谷氨酸以高光学纯度制备二脱氧核苷。活化的2，3-二脱氧戊呋喃糖酶与甲硅烷基化的嘌呤或嘧啶之间的缩合反应提供了可分离的双脱氧核苷的β/α混合物。

  DOI：

  10.1016/s0040-4039(00)80265-8
• 作为产物：
  描述：

  左旋葡萄糖酮 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 生成 (S)-5-(benzoyloxymethyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  A Method for Easy Preparation of Optically Pure (S)-5-Hydroxy-2-penten-4-olide and (S)-5-Hydroxypentan-4-olide

  摘要：

  DOI：

  10.3987/com-89-5300

文献信息

• METHOD FOR PRODUCING THIOLANE SKELETON-TYPE GLYCOCONJUGATE, AND THIOLANE SKELETON-TYPE GLYCOCONJUGATE
  申请人：FUJIFILM Corporation

  公开号：US20160355536A1

  公开（公告）日：2016-12-08

  There is provided a production method of a compound represented by the following formula (II) through a step of reacting a compound represented by the following General Formula (I) with a sulfur compound. In General Formulas (I) and (II), R 1 represents a hydrogen atom or an acyl group, R 2 represents a hydrogen atom, a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R 3 represents a hydrogen atom or an acyloxy group, R 5 represents an alkyl group or an aryl group, and X represents a leaving group. Here, in a case where R 2 is a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R 3 is an acyloxy group.

  提供了一种通过将通用式（I）表示的化合物与硫化合物反应的步骤来制备通式（II）表示的化合物的生产方法。在通式（I）和（II）中，R1代表氢原子或酰基，R2代表氢原子、氟原子、酰氧基、芳基甲氧基、烯丙氧基、芳基甲氧羰氧基或烯丙氧羰氧基，R3代表氢原子或酰氧基，R5代表烷基或芳基，X代表离去基团。在R2为氟原子、酰氧基、芳基甲氧基、烯丙氧基、芳基甲氧羰氧基或烯丙氧羰氧基的情况下，R3为酰氧基。
• Stereoselective Amination of 5-Substituted γ-Lactones and γ-Lactams – A Convenient Route for the Preparation of 5-Substituted (3S,5S)-3-Acetylaminotetrahydrofuran-2-ones and (3S,5S)-3-Acetylaminopyrrolidin-2-ones
  作者：Marko S'kof、Jurij Svete、Matej Kmetič、Simona Golič-Grdadolnik、Branko Stanovnik

  DOI：10.1002/(sici)1099-0690(199907)1999:7<1581::aid-ejoc1581>3.0.co;2-2

  日期：1999.7

  5-Substituted (S)-tetrahydrofuran-2-ones (1a,b) and (S)-pyrrolidin-2-ones (1c,d) were transformed in three steps, by treatment with tert-butoxybis(dimethylamino)methane (Bredereck's reagent), followed by nitrosation and stereoselective catalytic hydrogenation, into the corresponding 5-substituted (3S,5S)-3-acetylaminotetrahydrofuran-2-ones (4a,b) and (3S,5S)-3-acetylaminopyrrolidin-2-ones (4c,d).

  5-取代的 (S)-四氢呋喃-2-酮 (1a,b) 和 (S)-吡咯烷-2-酮 (1c,d) 通过用叔丁氧基双（二甲氨基）甲烷（Bredereck's试剂），然后进行亚硝化和立体选择性催化氢化，生成相应的 5-取代 (3S,5S)-3-乙酰氨基四氢呋喃-2-酮 (4a,b) 和 (3S,5S)-3-乙酰氨基吡咯烷-2-酮（ 4c，d）。
• Synthesis of (<i>S</i>)-3-heteroaryl-2-hydroxy-l-propyl benzoates by ‘ring switching’ methodology
  作者：Damjana Mihelič、Renata Jakše、Jurij Svete、Branko Stanovnik、Simona GoliČ Grdadolnik

  DOI：10.1002/jhet.5570380610

  日期：2001.11

  (S)-5-Benzoyloxymethyl-3-[(E)-(dimethylamino)methylidene]tetrahydrofuran-2-one (6), prepared in 5 steps from L-glutamic acid (1), was used as precursor in a one step ‘ring switching’ synthesis of (S)-2-hydroxy-3-heteroaryl-l-propyl benzoates 13-18, 23, 24. In the reaction of 6 with 2-aminopyridine (21) and 2-amino-4,6-dimethylpyrimidine (22) the corresponding dimethylamine substitution products (25

  由L-谷氨酸（1）分5步制备的（S）-5-苯甲酰氧基甲基-3-[（E）-（二甲基氨基）亚甲基]四氢呋喃-2-酮（6）在一步中用作前体（S）-2-羟基-3-杂芳基-1-丙基苯甲酸酯的“环交换”合成13-18，23，24.在6与2-氨基吡啶（21）和2-氨基-4,6的反应中-二甲基嘧啶（22），得到相应的二甲胺取代产物（25、26）。
• METHOD FOR PRODUCTING THIOLANE SKELETON-TYPE GLYCOCONJUGATE, AND THIOLANE SKELETON-TYPE GLYCOCONJUGATE
  申请人：FUJIFILM Corporation

  公开号：EP3109245A1

  公开（公告）日：2016-12-28

  There is provided a production method of a compound represented by the following formula (II) through a step of reacting a compound represented by the following General Formula (I) with a sulfur compound. In General Formulas (I) and (II), R1 represents a hydrogen atom or an acyl group, R2 represents a hydrogen atom, a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R3 represents a hydrogen atom or an acyloxy group, R5 represents an alkyl group or an aryl group, and X represents a leaving group. Here, in a case where R2 is a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R3 is an acyloxy group.

  本发明提供了一种下式(II)化合物的生产方法，其步骤是将下式(I)化合物与硫化合物反应。 在通式（I）和（II）中，R1 代表氢原子或酰基，R2 代表氢原子、氟原子、酰氧基、芳基甲基氧基、烯丙基氧基、芳基甲基氧基羰基氧基或烯丙基氧基羰基氧基，R3 代表氢原子或酰氧基，R5 代表烷基或芳基，X 代表离去基团。 这里，在 R2 是氟原子、酰氧基、芳基甲基氧基、烯丙基氧基、芳基甲基氧基羰基氧基或烯丙基氧基羰基氧基的情况下，R3 是酰氧基。
• Stereoselectivities in the Coupling Reaction between Silylated Pyrimidine Bases and 1-Halo-2,3-dideoxyribose
  作者：Hiroshi Kawakami、Takashi Ebata、Koshi Koseki、Katsuya Matsumoto、Hajime Matsushita、Yoshitake Naoi、Kazuo Itoh

  DOI：10.3987/com-90-5563

  日期：——

  Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines have been examined from the point of stereoselectivity. When the reaction was carried out in chloroform, the selectivity was in the anomeric ratio of alpha:beta = 4:6. On the other hand, the presence of tertiary amine raises the selectivity to alpha:beta = 3:7.