6-bromo-2,6-dideoxy-D-arabino-hexono-1,4-lactone | 71672-01-0

• 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: 6-bromo-2,6-dideoxy-D-arabino-hexono-1,4-lactone
• 英文别名: (4R,5S)-5-[(1S)-2-bromo-1-hydroxyethyl]-4-hydroxyoxolan-2-one
• CAS: 71672-01-0
• 化学式: C₆H₉BrO₄
• 分子量: 225.039
• InChiKey: BCAGVZZOCCCQBE-KODRXGBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-2,6-dideoxy-D-arabino-hexono-1,4-lactone 以 水 为溶剂， 反应 2.0h， 以61%的产率得到3,6-anhydro-2-deoxy-D-arabino-hexono-1,4-lactone
  参考文献：
  名称：

  Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors

  摘要：

  6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.

  DOI：

  10.1016/s0040-4020(01)89337-6
• 作为产物：
  描述：

  2,6-dibromo-2,6-dideoxy-D-mannono-1,4-lactone 在 溴 、 一水合肼 作用下， 生成 6-bromo-2,6-dideoxy-D-arabino-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

• The preparation of some bromodeoxy- and deoxy-hexoses from bromodeoxyaldonic acids
  作者：Klaus Bock、Inge Lundt、Christian Pedersen

  DOI：10.1016/s0008-6215(00)85607-4

  日期：1981.3

  Abstract The reduction of 2,6-dibromo-2,6-dideoxy- D -mannono- and 2,6-dibromo-2,6-dideoxy- D -glucono-1,4-lactone with sodium borohydride affords 2,6-dibromo-2,6-dideoxy- D -mannose and 2,6-dibromo-2,6-dideoxy- D -glucose, respectively, which may be isolated as their acetates. Similarly, 2-bromo-2,6-dideoxy- L- -glucono-1,4-lactone yields 2-bromo-2,6-dideoxy- L -glucose. Hydrogenolysis of 2,6-dibromo-2

  摘要用硼氢化钠还原2,6-二溴-2,6-二脱氧-D-甘露糖醛和2,6-二溴-2,6-二脱氧-D-葡糖醛-1,4-内酯可得到2,6-二溴-2,6-二脱氧-D-甘露糖和2,6-二溴-2,6-二脱氧-D-葡萄糖，它们可以作为乙酸盐被分离出来。类似地，2-溴-2,6-二脱氧-L-葡萄糖基-1,4-内酯产生2-溴-2,6-二脱氧-L-葡萄糖。2,6-二溴-2,6-二脱氧-D-甘露聚糖-1,4-内酯的氢解反应产生6-溴-2,6-二脱氧-D-阿拉伯糖-己酮-1,4-内酯，随后为2 ，6-二脱氧-D-阿拉伯糖-己烯-1，4-内酯。用双（1,2-二甲基丙基）硼烷还原后者可得到2,6-二脱氧-D-阿拉伯糖基己糖，可将其转化为甲基2,6-二脱氧-3,4-二-O-p-硝基苯甲酰基-D-阿拉伯糖基-己吡喃糖苷。
• 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。
• Preparation of Enantiomerically Pure Mono- and Diepoxylactones from Aldonolactones
  作者：Inge Lundt、Christian Pedersen

  DOI：10.1055/s-1992-26196

  日期：——

  Treatment of bromodeoxyaldonolactones with a nonaqueous base, such as potassium fluoride, caesium fluoride or potassium carbonate in acetone, yields 2,3-anhydro-, 5,6-anhydro-, and 2,3: 5,6-dianhydrohexonolactones, or 2,3-anhydro-and 2,3:6,7-dianhydrohepto-nolactones in good yields.

  用非水基（如丙酮中的氟化钾、氟化铯或碳酸钾）处理溴代脱氧己内酯，可得到 2,3-脱水、5,6-脱水和 2,3：5,6-二氢己内酯或 2,3-脱水-2,3:6,7-二氢七内酯，收率良好。
• 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。