Methyl 3-deoxy-3-fluoro-β-D-arabinofuranoside | 152711-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: Methyl 3-deoxy-3-fluoro-β-D-arabinofuranoside
• 英文别名: 1-O-methyl-3-deoxy-3-fluoro-β-D-arabinofuranose；(2R,3R,4S,5R)-4-fluoro-5-(hydroxymethyl)-2-methoxyoxolan-3-ol
• CAS: 152711-00-7
• 化学式: C₆H₁₁FO₄
• 分子量: 166.149
• InChiKey: WHDQETPTRMZQRD-ARQDHWQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-deoxy-3-fluoro-β-D-arabinofuranoside 在 吡啶 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 氨 、 氢溴酸 、 三正丁基氢锡 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 48.0h， 生成 3’-脱氧-3-氟胸苷
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxy-3′-fluorothymidine Using Individual Anomers of 1,5-Di-O-benzoyl-2,3-dideoxy-3-fluoro-D-erythro-pentofuranose as Glycosylating Agents

  摘要：

  描述了一种方便的制备1,5-二-O-苯甲酰基-2,3-去氧-3-氟-D-赤糖戊呋喃糖的α-和β-异构体的方法。每种异构体作为糖苷化试剂，与双三甲基硅基化胸腺嘧啶在三甲基硅基三氟甲磺酸的存在下进行反应。 在最佳条件下，2′,3′-去氧-3′-氟胸腺苷（FLT）及其α-异构体的产率分别为64%和25%。

  DOI：

  10.1055/s-1993-25925
• 作为产物：
  描述：

  Methyl-2-O-tosyl-β-D-xylofuranosid 在 potassium hydrogen bifluoride 、 sodium methylate 、 sodium fluoride 作用下， 以 甲醇 、 乙二醇 为溶剂， 生成 Methyl 3-deoxy-3-fluoro-β-D-arabinofuranoside
  参考文献：
  名称：

  Design and Synthesis of A₃Adenosine Receptor Ligands, 3′-Fluoro Analogues of Cl-IB-MECA

  摘要：

  Synthesis of 3'-deoxy-3'-fluoro-N-6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A(3) adenosine receptor are described.

  DOI：

  10.1081/ncn-120022701

文献信息

• A new synthesis of 3′‐deoxy‐3′‐fluoroadenosine, a key intermediate of cyclic dinucleotide
  作者：Yayun Qiu、Zixing Li、Fangmin Ning、Dandan Tang、Huansheng Chen

  DOI：10.1002/jhet.4751

  日期：2024.1

  A new synthesis of 3′-deoxy-3′-fluoroadenosine for use as an important intermediate of antitumor-active cyclic dinucleotide is disclosed. The synthesis started with the known 5-O-TBDPS-D-lyxofuranose 1,2-acetonides, which was first transformed into a fluorinated compound after the DAST reaction. Desilylation and acidic methanolysis were then finished in one pot. After a sequence of triflation, displacement

  公开了用作抗肿瘤活性环状二核苷酸的重要中间体的3'-脱氧-3'-氟腺苷的新合成。合成从已知的 5- O -TBDPS-D-呋喃来糖 1,2-丙酮化合物开始，在 DAST 反应后首先将其转化为氟化化合物。然后脱甲硅烷基化和酸性甲醇解在一锅中完成。经过一系列三氟甲磺酸化、OBz置换以及苯甲酰化，得到过苯甲酰化的3-脱氧-3-氟-D-呋喃核苷，将其转化为3'-脱氧-3'-氟腺苷，作为环状二核苷酸的关键中间体氨解后。
• Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands
  作者：Moo Hong Lim、Hea Ok Kim、Hyung Ryong Moon、Seung Jin Lee、Moon Woo Chun、Zhan-Guo Gao、Neli Melman、Kenneth A Jacobson、Joong Hyup Kim、Lak Shin Jeong

  DOI：10.1016/s0960-894x(03)00027-1

  日期：2003.3

  Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) adenosine receptor, the corresponding 3-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Design and Synthesis of A₃Adenosine Receptor Ligands, 3′-Fluoro Analogues of Cl-IB-MECA
  作者：Hea Ok Kim、Moo Hong Lim、Jae Gyu Park、Hyung Ryong Moon、Kenneth A. Jacobson、Hee-Doo Kim、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1081/ncn-120022701

  日期：2003.10

  Synthesis of 3'-deoxy-3'-fluoro-N-6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A(3) adenosine receptor are described.
• Synthesis of 2′,3′-Dideoxy-3′-fluorothymidine Using Individual Anomers of 1,5-Di-<i>O</i>-benzoyl-2,3-dideoxy-3-fluoro-D-<i>erythro</i>-pentofuranose as Glycosylating Agents
  作者：Igor A. Mikhailopulo、Tamara I. Pricota、Nicolai E. Poopeiko、Tatjana V. Klenitskaya、Natalia B. Khripach

  DOI：10.1055/s-1993-25925

  日期：——

  A convenient preparation of α- and β-anomers of 1,5-di-O-benzoyl-2, 3-dideoxy-3-fluoro-D-erythro-pentofuranose is described. Each anomer is studied as the glycosylating agent in the reaction with bis-trimethylsilylated thymine in the presence of trimethylsilyl triflate. Under optimum conditions, 2′,3′-dideoxy-3′-fluorothymidine (FLT) and its α-anomer are isolated in 64 and 25% yields, respectively.

  描述了一种方便的制备1,5-二-O-苯甲酰基-2,3-去氧-3-氟-D-赤糖戊呋喃糖的α-和β-异构体的方法。每种异构体作为糖苷化试剂，与双三甲基硅基化胸腺嘧啶在三甲基硅基三氟甲磺酸的存在下进行反应。 在最佳条件下，2′,3′-去氧-3′-氟胸腺苷（FLT）及其α-异构体的产率分别为64%和25%。