2-deoxy-D-lyxo-hexono-1,4-lactone | 61653-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-deoxy-D-lyxo-hexono-1,4-lactone
• 英文别名: (4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxyoxolan-2-one
• CAS: 61653-41-6
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: WIKTYYPIOVPRBF-ZMIZWQJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-deoxy-D-lyxo-hexono-1,4-lactone 在 一水合肼 作用下， 以 甲醇 为溶剂， 以68%的产率得到2-deoxy-L-ribo-hexonic acid hydrazide
  参考文献：
  名称：

  The Base Catalyzed Rearrangement of Some 6-Bromo-2,6-dideoxyaldono-1,4-lactones. Preparation of L-Digitoxose.

  摘要：

  DOI：

  10.3891/acta.chem.scand.38b-0555
• 作为产物：
  描述：

  2,6-dibromo-2,6-dideoxy-D-mannono-1,4-lactone 在 盐酸 、 溴 、 potassium carbonate 、 一水合肼 作用下， 反应 2.0h， 生成 2-deoxy-D-lyxo-hexono-1,4-lactone
  参考文献：
  名称：

  The Base Catalyzed Rearrangement of Some 6-Bromo-2,6-dideoxyaldono-1,4-lactones. Preparation of L-Digitoxose.

  摘要：

  DOI：

  10.3891/acta.chem.scand.38b-0555

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。
• C1 Oxidation/C2 Reduction Isomerization of Unprotected Aldoses Induced by Light/Ketone
  作者：Yusuke Masuda、Hiromu Tsuda、Masahiro Murakami

  DOI：10.1002/anie.201914242

  日期：2020.2.10

  Unprotected aldoses in water undergo an isomerization reaction via a radical pathway when irradiated with light in the presence of water-soluble benzophenone. Whereas its anomeric carbon (C1) is oxidized to a carboxy group, the hydroxy group on the C2 carbon is replaced by hydrogen. The generated 2-deoxy lactones are readily reduced to the corresponding 2-deoxy aldoses, which are often contained in

  当在水溶性二苯甲酮存在下用光照射时，水中未保护的醛糖会通过自由基途径经历异构化反应。而其异头碳（C1）被氧化成羧基，而C2碳上的羟基被氢取代。产生的2-脱氧内酯很容易还原为相应的2-脱氧醛糖，通常包含在生物活性化合物中。
• Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone
  作者：Andrea Bordoni、Rosa M. de Lederkremer、Carla Marino

  DOI：10.1016/j.carres.2006.04.012

  日期：2006.8

  A photoinduced electron-transfer (PET) reaction was used for the deoxygenation at C-2 of aldonolactones derivatized as 2-O-[3-(trifluoromethyl)benzoyl] or benzoyl esters. By irradiation of different D-galactono- and D-glucono-1,4-derivatives, with a 450W lamp, using 9-methylcarbazole as photosensitizer, the corresponding 2-deoxy-D-lyxo- and 2-deoxy-D-arabino-hexono-1,4-lactones were efficiently obtained

  光致电子转移（PET）反应用于衍生为2-O- [3-（三氟甲基）苯甲酰基]或苯甲酰基酯的烯醇内酯在C-2处的脱氧。通过使用9-甲基咔唑作为光敏剂，用450W灯照射不同的D-半乳糖基和D-葡萄糖基1,4-衍生物，相应的2-deoxy-D-lyxo-和2-deoxy-D-arabino-有效地获得了六邻体-1,4-内酯。
• Photoinduced electron transfer and chemical α-deoxygenation of d-galactono-1,4-lactone. Synthesis of 2-deoxy-d-lyxo-hexofuranosides
  作者：Alejandro Chiocconi、Carla Marino、Eugenio Otal、Rosa M de Lederkremer

  DOI：10.1016/s0008-6215(02)00118-0

  日期：2002.11

  Two simple procedures for the synthesis of 2-deoxy-D-lyxo-hexono-1,4-lactone are described. Reductive cleavage of a 2-O-tosyl derivative of D-galactono-1,4-lactone in the presence of sodium iodide afforded the 2-deoxy derivative. On the other hand, alpha-deoxygenation of D-galactono-1,4-lactone was easily achieved by photochemical electron transfer deoxygenation of HO-2 as the 3-(trifluoromethyl)benzoate

  描述了两个简单的合成2-脱氧-D-lyxo-六邻--1,4-内酯的程序。在碘化钠的存在下，D-半乳糖-1，4-内酯的2-O-甲苯磺酰基衍生物的还原裂解得到2-脱氧衍生物。另一方面，通过将HO-2作为3-（三氟甲基）苯甲酸酯进行光化学电子转移脱氧，可以容易地实现D-半乳糖-1,4-内酯的α-脱氧。合成了甲基2-脱氧-β-D-lyxo-六呋喃糖苷（“甲基2-脱氧-β-D-半乳糖呋喃糖苷”），并测试了其作为来自腐霉青霉的exoβ-D-半乳糖苷酶的底物。在反应之后进行HPAEC，显示2-脱氧-β-D-D-半乳糖呋喃糖苷甲基未通过与酶温育而水解。2-脱氧内酯 2-脱氧-β-D-半乳糖呋喃糖苷也不能充当与4-硝基苯基β-D-半乳糖醛糖苷反应的抑制剂。目前和我们以前的结果表明，半乳糖呋喃糖苷的C-2，C-3和C-6处的羟基对于与外切β-D-半乳糖醛酸苷酶的相互作用至关重要。
• Overend et al., Journal of the Chemical Society, 1950, p. 671,676
  作者：Overend et al.

  DOI：——

  日期：——