1β-(thiophen-2-yl)-1,2-dideoxy-D-ribofuranose | 170079-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1β-(thiophen-2-yl)-1,2-dideoxy-D-ribofuranose
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-thiophen-2-yloxolan-3-ol
• CAS: 170079-34-2
• 化学式: C₉H₁₂O₃S
• 分子量: 200.258
• InChiKey: UBUYJUIWJCDRLP-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1β-(thiophen-2-yl)-1,2-dideoxy-D-ribofuranose 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-thiophen-2-yl-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Stability and Selectivity of Unnatural DNA with Five-Membered-Ring Nucleobase Analogues

  摘要：

  In an effort to develop an orthogonal third base pair for the storage of genetic information, thiophene and furan heterocycles have been examined as nucleobase analogues. The stability of the unnatural bases was evaluated in duplex DNA paired opposite other unnatural bases as well as opposite the natural bases. Several unnatural base pairs are identified that are both reasonably stable and strongly selective against mispairing with native bases. These results expand the potential nucleobase analogues with which the genetic alphabet may be expanded to include five-membered-ring heterocycles.

  DOI：

  10.1021/ja012090t
• 作为产物：
  描述：

  2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-erythropentofuranose 在 正丁基锂 、 4 A molecular sieve 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1β-(thiophen-2-yl)-1,2-dideoxy-D-ribofuranose
  参考文献：
  名称：

  Stability and Selectivity of Unnatural DNA with Five-Membered-Ring Nucleobase Analogues

  摘要：

  In an effort to develop an orthogonal third base pair for the storage of genetic information, thiophene and furan heterocycles have been examined as nucleobase analogues. The stability of the unnatural bases was evaluated in duplex DNA paired opposite other unnatural bases as well as opposite the natural bases. Several unnatural base pairs are identified that are both reasonably stable and strongly selective against mispairing with native bases. These results expand the potential nucleobase analogues with which the genetic alphabet may be expanded to include five-membered-ring heterocycles.

  DOI：

  10.1021/ja012090t

文献信息

• Modular Synthesis of 5-Substituted Thiophen-2-yl <i>C</i>-2′-Deoxyribonucleosides
  作者：Jan Bárta、Radek Pohl、Blanka Klepetářová、Nikolaus P. Ernsting、Michal Hocek

  DOI：10.1021/jo800177y

  日期：2008.5.1

  A new modular methodology of preparation of 5-substituted thiophene-2-yl C-nucleosides was developed. A Friedel−Crafts-type of C-glycosidation of 2-bromothiophene with toluoyl-protected methylglycoside 2 gave the desired protected 1β-(5-bromothiophen-2-yl)-1,2-dideoxyribofuranose 4a in 60%. The key intermediate 4a was then subjected to a series of palladium-catalyzed cross-coupling reactions. The cross-coupling

  开发了一种新的制备5-取代的噻吩-2-基C-核苷的模块化方法。弗里德尔-克拉夫茨型2-溴噻吩与对甲苯甲酰基保护的甲基苷的C-糖苷化的2得到所需保护的1β-（5-溴噻吩-2-基）-1,2- dideoxyribofuranose 4A在60％以上。然后使关键中间体4a经历一系列钯催化的交叉偶联反应。与烷基有机金属的交叉偶联反应得到β-​​（5-烷基噻吩-2-基）-2-脱氧核糖核苷4和7产量中等，伴有减少的副产品。另一方面，与芳基斯坦酮的交叉偶联进展顺利，以高收率得到一系列β-（5-芳基噻吩-2-基）-2-脱氧核糖核苷4。NaMeOH在MeOH中对甲苯甲酰化核苷的脱保护，以及Et 3 N·3HF对甲硅烷基化的核苷的脱保护得到一系列游离的C-核苷6。或者，通过未保护的1β-（5-溴噻吩-2-基）-1，2-二脱氧核糖呋喃糖与硼酸的水相交叉偶联反应，一步制备其它类型的5-芳基噻吩C-核苷6。标题5-芳基噻吩C-核苷6
• Synthesis of C-Deoxyribonucleosides Bearing Typical Aromatic Heterocycles as Base Moiety
  作者：Masataka Yokoyama、Takahiro Akiba、Hideo Togo

  DOI：10.1055/s-1995-3969

  日期：1995.6

  Seven C-2-deoxy-D- ribonucleosides bearing typical aromatic heterocycles as base moiety are synthesized in good yields by the stereoselective addition of lithium salts of aromatic heterocycles to the silyl-protected 2-deoxy-D-ribose followed by cyclization and deprotection.

  通过将芳香杂环的锂盐与硅烷保护的 2-脱氧-D-核糖进行立体选择性加成，然后进行环化和脱保护，以良好的产率合成了七种以典型芳香杂环为基团的 C-2-脱氧-D-核糖核苷。
• Stability and Selectivity of Unnatural DNA with Five-Membered-Ring Nucleobase Analogues
  作者：Markus Berger、Scott D. Luzzi、Allison A. Henry、Floyd E. Romesberg

  DOI：10.1021/ja012090t

  日期：2002.2.1

  In an effort to develop an orthogonal third base pair for the storage of genetic information, thiophene and furan heterocycles have been examined as nucleobase analogues. The stability of the unnatural bases was evaluated in duplex DNA paired opposite other unnatural bases as well as opposite the natural bases. Several unnatural base pairs are identified that are both reasonably stable and strongly selective against mispairing with native bases. These results expand the potential nucleobase analogues with which the genetic alphabet may be expanded to include five-membered-ring heterocycles.