9-β-L-xylo-furanosyladenine | 154568-82-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-β-L-xylo-furanosyladenine
• 英文别名: 1-(6-amino-purin-9-yl)-β-D-1-deoxy-xylofuranose；9-(β-L-Xylofuranosyl)adenine；9-β-D-Xylofuranosyladenin；Adenin-Arabinosid；(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 154568-82-8
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: OIRDTQYFTABQOQ-HUEBKHCJSA-N

物化性质

• 沸点：
  676.3±65.0 °C(Predicted)
• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-β-L-xylo-furanosyladenine 在 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 生成 L-adenosine
  参考文献：
  名称：

  A New and Convenient Approach for the Synthesis of Ribo- and 2′-Deoxyribo-β-L-Furanonucleosides Starting From β-L-Xylofuranonucleosides

  摘要：

  Ribo- and 2'-deoxyribo-beta-L-furanosyladenine have been synthesized. Although these compounds have been already reported in the literature, it seemed to us that a more convenient approach for their synthesis deserved to be developed. Intramolecular substitution as well as Mitsunobu reaction were used to invert the configuration of carbon 3' of starting beta-L-xylofuranosyl intermediates.

  DOI：

  10.1080/15257779908041512
• 作为产物：
  描述：

  1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranose 在 氨 、 四氯化锡 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 9-β-L-xylo-furanosyladenine
  参考文献：
  名称：

  合成和β-L-的抗病毒评价低聚木糖五个-fuanosyl核苷天然存在的核酸碱基†

  摘要：

  已经合成了天然存在的核苷的β-L-二甲苯基-呋喃糖基类似物，并研究了它们的抗病毒特性。迄今为止，所有这些化合物都是未知的，它们是通过嘧啶和嘌呤糖苷配基与合适的过酰基-L-木糖-呋喃糖（为达到我们目前的目的特别从L-木糖合成）进行糖基化立体定向制备的，然后除去保护基团。测试了所有制备的化合物对多种DNA和RNA病毒（包括HIV）的活性，但它们未显示出显着的抗病毒活性。

  DOI：

  10.1002/jhet.5570300510

文献信息

• 2'-deoxy-L-nucleosides
  申请人：Watanabe Kyoichi

  公开号：US20050090660A1

  公开（公告）日：2005-04-28

  This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH 2 , NHR′, or NR′R″ Z is H, F, Cl, Br, I, CN, or NH 2 . R is hydrogen, halogen, lower alkyl of C 1 -C 6 or aralkyl, NO 2 , NH 2 , NHR′, NR′R″, OH, OR, SH, SR, CN, CONH 2 , CSNH 2 , CO 2 H, CO 2 R′, CH 2 CO 2 H, CH 2 CO 2 R′, CH═CHR, CH 2 CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C 1 -C 6 . R 13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

  这项发明提供了制备具有以下结构的化合物的方法： 其中 X和Y相同或不同，且H、OH、OR、SH、SR、NH2、NHR′或NR′R″ Z为H、F、Cl、Br、I、CN或NH2 R为氢、卤素、C1-C6的低碳烷基或芳基烷基、NO2、NH2、NHR′、NR′R″、OH、OR、SH、SR、CN、CONH2、CSNH2、CO2H、CO2R′、CH2CO2H、CH2CO2R′、CH═CHR、CH2CH═CHR或C═CR。 R′和R″相同或不同，且为C1-C6的低碳烷基。 R13为氢、烷基、酰基、磷酸酯（单磷酸酯、二磷酸酯、三磷酸酯或稳定磷酸酯）或硅基。
• Synthesis of 2'-deoxy-l-nucleosides
  申请人：Pharmasset Limited

  公开号：EP1600451A2

  公开（公告）日：2005-11-30

  The present invention provides a process for the preparation of a 2'-deoxy-L-nucleoside comprising the steps of: a) preparing a 2'-halo-L-nucleoside of the following formula:    wherein B is a heterocyclic or heteroaromatic base, R8 and R9 are independently hydrogen or a suitable protecting group, V is a halogen; and b) reducing the 2'-halo-L-nucleoside to a 2'-deoxy-L-nucleoside.

  本发明提供了一种制备 2'-脱氧-L-核苷的工艺，包括以下步骤： a) 制备下式的 2'-卤代-L-核苷： 其中 B 是杂环或杂芳族基团，R8 和 R9 独立地为氢或合适的保护基团，V 是卤素；以及 b) 将 2'-卤代-L-核苷还原成 2'-脱氧-L-核苷。
• Synthesis of 2'-deoxy-L-nucleosides
  申请人：Pharmasset Limited

  公开号：EP1600452A2

  公开（公告）日：2005-11-30

  The present invention provides a process for the preparation of a 2'-deoxy-L-nucleoside comprising the following steps: a) preparing from a suitably protected and activated L-furanose a 2-S-substituted-2-deoxy-L-furanose of the following formula: wherein B is a heterocyclic or heteroaromatic base, R8 and R9 are independently hydrogen or a suitable protecting group; R7 is a suitable protecting group; b) cyclizing the 2-S-substituted-2-deoxy-L-furanose to form a cyclonucleoside of the following formula: and c) reducing the cyclonucleoside to a 2'-deoxy-L-nucleoside.

  本发明提供了一种制备 2'-脱氧-L-核苷的工艺，包括以下步骤： a) 由适当保护和活化的 L-呋喃糖制备下式的 2-S-取代的-2-脱氧-L-呋喃糖： 其中 B 是杂环基或杂芳香基，R8 和 R9 独立地为氢或合适的保护基团；R7 是合适的保护基团； b) 环化 2-S-取代的-2-脱氧-L-呋喃糖，形成下式的环核苷： 和 c) 将环核苷还原成 2'-脱氧-L-核苷。
• Synthesis and antiviral evaluation of β-L-<i>Xylo</i>-fuanosyl nucleosides of the five naturally occurring nucleic acid bases
  作者：Gilles Gosselin、Marie-Christine Bergogne、Jean-Louis Imbach

  DOI：10.1002/jhet.5570300510

  日期：1993.10

  The β-L-xylo-furanosyl analogues of the naturally occurring nucleosides have been synthesized and their antiviral properties examined. All these compounds were hitherto unknown and they were stereospecifically prepared by glycosylation of pyrimidine and purine aglycons with a suitably peracyl-L-xylo-furanose (specially synthesized from L-xylose for our present purpose), followed by removal of the protecting

  已经合成了天然存在的核苷的β-L-二甲苯基-呋喃糖基类似物，并研究了它们的抗病毒特性。迄今为止，所有这些化合物都是未知的，它们是通过嘧啶和嘌呤糖苷配基与合适的过酰基-L-木糖-呋喃糖（为达到我们目前的目的特别从L-木糖合成）进行糖基化立体定向制备的，然后除去保护基团。测试了所有制备的化合物对多种DNA和RNA病毒（包括HIV）的活性，但它们未显示出显着的抗病毒活性。
• A New and Convenient Approach for the Synthesis of Ribo- and 2′-Deoxyribo-β-L-Furanonucleosides Starting From β-L-Xylofuranonucleosides
  作者：V. Boudou、G. Gosselin、J-L. Imbach

  DOI：10.1080/15257779908041512

  日期：1999.4

  Ribo- and 2'-deoxyribo-beta-L-furanosyladenine have been synthesized. Although these compounds have been already reported in the literature, it seemed to us that a more convenient approach for their synthesis deserved to be developed. Intramolecular substitution as well as Mitsunobu reaction were used to invert the configuration of carbon 3' of starting beta-L-xylofuranosyl intermediates.