2-deoxy-2,2-difluoro-D-ribose | 95058-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2,2-difluoro-D-ribose
• 英文别名: 2'-deoxy-2',2'-difluoro-D-ribofuranose；2-deoxy-2,2-difluoro-D-ribofuranose；(4R,5R)-3,3-difluoro-5-(hydroxymethyl)oxolane-2,4-diol
• CAS: 95058-90-5
• 化学式: C₅H₈F₂O₄
• 分子量: 170.113
• InChiKey: LDHXMQXUOUZOLF-HERZVMAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-deoxy-2,2-difluoro-D-ribose 、 乙酰氯 在 4-二甲氨基吡啶 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-deoxy-2,2-difluoro-1,3,5-triacetyl-D-ribofuranose
  参考文献：
  名称：

  Method for preparation of 2'-deoxy-2', 2'-difluoro-beta-cytidine or pharmaceutically acceptable salts thereof by using 1,6-anhydro-beta-D-glucose as raw material

  摘要：

  本发明提供了一种制备2'-去氧-2',2'-二氟-β-胞苷或其药学上可接受的盐的方法，包括以1,6-脱水-β-D-葡萄糖为原料，经氧化和氟化得到2-去氧-2,2-二氟-D-核糖呋喃糖作为中间体。最终从2-去氧-2,2-二氟-D-核糖呋喃糖的中间体制备出2'-去氧-2',2'-二氟-β-胞苷。该方法操作简单，产率高，能有效地用于大规模生产。

  公开号：

  US20060003963A1
• 作为产物：
  描述：

  2-deoxy-2,2-difluoro-1-oxoribose 在 2,6-二甲基吡啶 、 氢溴酸 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 2-deoxy-2,2-difluoro-D-ribose
  参考文献：
  名称：

  Synthesis of 2-deoxy-2,2-difluoro-D-ribose and 2-deoxy-2,2'-difluoro-D-ribofuranosyl nucleosides

  摘要：

  DOI：

  10.1021/jo00246a002

文献信息

• Process of making an alpha-anomer enriched 2-deoxy-2,2-diflouro-d-ribofuranosyl sulfonate and use thereof for making a beta nucleoside
  申请人：Wang Lung-Hu

  公开号：US20060276638A1

  公开（公告）日：2006-12-07

  A process of preparing an alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate, which is useful as an intermediate in the preparation of a beta nucleoside, such as gemcitabine, an anti-tumor agent. A beta-2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate is heated and converted to an alpha-2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate in the absence of an effective amount of a sulfonate salt to facilitate the conversion. In addition, an anomeric mixture of an alpha-anomer and a beta-anomer of 2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate can be dissolved in a mixture of water and a solvent and heated to produce a lactol, which may be further converted to an alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate.

  制备α型富集2-脱氧-2,2-二氟-D-核糖基磺酸的过程，该化合物可用作β-核苷类似物的中间体，例如抗肿瘤药物吉西他滨。将β-2-脱氧-2,2-二氟-D-核糖基磺酸在缺乏足够量的磺酸盐催化剂的情况下加热并转化为α-2-脱氧-2,2-二氟-D-核糖基磺酸。此外，α型异构体和β型异构体的2-脱氧-2,2-二氟-D-核糖基磺酸混合物可以溶解在水和溶剂的混合物中加热生成内酯，进一步转化为α型富集2-脱氧-2,2-二氟-D-核糖基磺酸。
• HERTEL, L. W.;KROIN, J. S.;MISNER, J. W.;TUSTIN, J. M., J. ORG. CHEM., 53,(1988) N 11, 2406-2409
  作者：HERTEL, L. W.、KROIN, J. S.、MISNER, J. W.、TUSTIN, J. M.

  DOI：——

  日期：——
• Synthesis of 2-deoxy-2,2-difluoro-D-ribose and 2-deoxy-2,2'-difluoro-D-ribofuranosyl nucleosides
  作者：L. W. Hertel、J. S. Kroin、J. W. Misner、J. M. Tustin

  DOI：10.1021/jo00246a002

  日期：1988.5
• Method for preparation of 2'-deoxy-2', 2'-difluoro-beta-cytidine or pharmaceutically acceptable salts thereof by using 1,6-anhydro-beta-D-glucose as raw material
  申请人：Gong Chen

  公开号：US20060003963A1

  公开（公告）日：2006-01-05

  The present invention provides a method for preparation of 2′-deoxy-2′,2′-difluoro-β-cytidine or pharmaceutically acceptable salt thereof, comprising starting from 1,6-anhydro-β-D-glucose as raw material, oxidizing, and fluorinating to obtain 2-deoxy-2,2-difluoro-D-ribofuranose as intermediate. The 2′-deoxy-2′,2′-difluoro-β-cytidine was finally prepared from the intermediate of 2-deoxy-2,2-difluoro-D-ribofuranose. The method is simple in operation and has a high yield. The method can effectively be used in large-scale production.

  本发明提供了一种制备2'-去氧-2',2'-二氟-β-胞苷或其药学上可接受的盐的方法，包括以1,6-脱水-β-D-葡萄糖为原料，经氧化和氟化得到2-去氧-2,2-二氟-D-核糖呋喃糖作为中间体。最终从2-去氧-2,2-二氟-D-核糖呋喃糖的中间体制备出2'-去氧-2',2'-二氟-β-胞苷。该方法操作简单，产率高，能有效地用于大规模生产。