1-chloro-2-deoxy-3,5-di-O-p-methylbenzeneformyl-L-ribofuranose | 141846-57-3

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 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: 1-chloro-2-deoxy-3,5-di-O-p-methylbenzeneformyl-L-ribofuranose
• 英文别名: 2-deoxy-3,5-di-O-p-toluoyl-L-erythro-pentofuranosyl chloride；1-chloro-3,5-ditoluoyl-2-deoxy-α-L-ribose；1-Chloro-2-deoxy-3,5-di-O-toluoyl-L-ribofuranose；[(2S,3R)-5-chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 141846-57-3
• 化学式: C₂₁H₂₁ClO₅
• 分子量: 388.848
• InChiKey: FJHSYOMVMMNQJQ-YTYFACEESA-N

物化性质

• 熔点：
  117-119°C
• 沸点：
  518.4±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、二氯甲烷（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  -20°C 冰箱

反应信息

• 作为反应物：
  描述：

  1-chloro-2-deoxy-3,5-di-O-p-methylbenzeneformyl-L-ribofuranose 在 bis-triphenylphosphine-palladium(II) chloride 、 N,O-双三甲硅基乙酰胺 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 1,2-二氯乙烷 为溶剂， 反应 16.5h， 生成 (2S,3R,5S)-5-(4-amino-5-(furan-2-yl)-2-oxopyrimidin-1(2H)-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate
  参考文献：
  名称：

  WO2023/225042

  摘要：

  公开号：
• 作为产物：
  描述：

  甲基-2-脱氧-L-赤式戊呋喃糖 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 吡啶盐酸盐 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲基叔丁基醚 为溶剂， 生成 1-chloro-2-deoxy-3,5-di-O-p-methylbenzeneformyl-L-ribofuranose
  参考文献：
  名称：

  一种高纯度替比夫定化合物的制备方法

  摘要：

  本发明属于医药技术领域，提供一种高纯度替比夫定化合物的制备方法，包括以LTD-4化合物为原料，与经硅化保护的胸腺嘧啶反应，可得中间体LTD-5化合物，其再经脱保护反应，经后处理得到所述替比夫定化合物。其中用MeONa作为脱保护反应的碱试剂，强酸性树脂作为除碱试剂。本发明简化了生产工艺，各步收率较高，得到了纯度及收率均较高的目标产物。

  公开号：

  CN105985393A

文献信息

• Synthesis of beta-L-2'-deoxy nucleosides
  申请人：Storer Richard

  公开号：US20050059632A1

  公开（公告）日：2005-03-17

  An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro- 1 -furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  提供了一种改进的2'-改性核苷和2'-脱氧核苷的制备工艺，例如，β-L-2'-脱氧胸苷（LdT）。特别是，改进的工艺针对的是2'-脱氧核苷的合成，该合成可能使用不同的起始材料，但都通过氯糖中间体或通过2,2'-脱水-1-呋喃糖核苷中间体进行。当使用2,2'-脱水-1-呋喃糖碱基中间体时，会采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚），它们能引起分子内位移反应，并形成所需核苷产品的高收率。本发明的一种替代工艺使用2,2'-脱水-1-呋喃糖碱基中间体而不使用隔离剂，也能以高收率获得2'-脱氧核苷。根据本发明制成的化合物可以作为制备其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• Production method of 2-deoxy-L-ribose compound
  申请人：Ajinomoto Co., Inc.

  公开号：EP1574515A3

  公开（公告）日：2007-05-23

  An aldehyde compound represented by the formula (1) is reacted with an organometallic compound represented by the formula (2) to give an alcohol compound represented by the formula (3), which is then subjected to deprotection of a hydroxyl group and production of aldehyde by acid hydrolysis. wherein R1 and R2 are each independently a hydroxyl-protecting group or R1 and R2 in combination show a hydroxyl-protecting group, R3 and R4 are each independently an alkyl group, an aralkyl group, an aryl group or a silyl group or R3 and R4 in combination show a cyclic alkyl group.

  化学反应方程式如下：化合物（1）表示的醛类化合物与化合物（2）表示的有机金属化合物反应，生成化合物（3）表示的醇类化合物，然后通过酸水解去保护羟基并生成醛类化合物。其中，R1和R2各自独立地是羟基保护基或R1和R2组合显示出羟基保护基，R3和R4各自独立地是烷基、芳基烷基、芳基或硅基，或者R3和R4组合显示出环状烷基。
• Synthesis of beta-L-2-Deoxy nucleosides
  申请人：Novartis AG

  公开号：EP2157095A2

  公开（公告）日：2010-02-24

  An improved process for the preparation of 2'-modified nucleosides and 2'-deoxynucleosides, such as, β-L-2'-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2'-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2' anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2'-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2'-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2'-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  本发明提供了一种改进的方法，用于制备2'-修饰核苷和2'-去氧核苷，例如β-L-2'-去氧胸腺嘧啶（LdT）。特别是，改进的方法针对合成一种2'-去氧核苷，该方法可以利用不同的起始材料，但是通过氯代糖中间体或2,2'无水-1-呋喃基-核碱中间体进行。当使用2,2'-无水-1-呋喃基碱中间体时，采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚），引起分子内位移反应并形成所需的核苷产物，产率良好。本发明的另一种替代方法利用无隔离剂的2,2'-无水-1-呋喃基碱中间体，以获得良好的2'-去氧核苷收率。根据本发明制备的化合物可以用作制备其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• [EN] SYNTHESIS OF beta-L-2-DEOXY NUCLEOSIDES<br/>[FR] SYNTHESE DE NUCLEOSIDES 20050113See references of EP 1639121A4
  申请人：IDENIX CAYMAN LTD

  公开号：WO2005003374A2

  公开（公告）日：2005-01-13

  An improved process for the preparation of 2'-modified nucleosides and 2'-deoxy-nucleosides, such as, β-L-2'-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2'-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2'­ anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2'-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2'-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2'-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  提供了一种改进的制备2'-修饰核苷和2'-脱氧核苷（例如β-L-2'-脱氧胸腺嘧啶（LdT））的方法。特别是，改进的方法是针对合成2'-脱氧核苷的，可以利用不同的起始材料，但是通过氯代糖中间体或2,2'-无水-1-呋喃核碱中间体进行。当使用2,2'-无水-1-呋喃基中间体时，采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚）引起分子内置换反应并形成所需的核苷产物，产率较高。本发明的另一种替代方法利用2,2'-无水-1-呋喃基中间体而不使用隔离剂，可以获得产率较高的2'-脱氧核苷。根据本发明制备的化合物可以用作其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• TUMOR TARGETING WITH L-ENANTIOMERIC OLIGONUCLEOTIDE CONJUGATES OF IMMUNOREAGENTS AND OF CHELATED RADIONUCLIDES
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0691981A1

  公开（公告）日：1996-01-17