1-(3,5-O-Isopropylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine | 99018-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(3,5-O-Isopropylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-(3',5'-O-Isopropyliden-β-D-2'-desoxy-threo-pentofuranosyl)-thymin；1-(O³,O⁵-isopropylidene-β-D-threo-2-deoxy-pentofuranosyl)-5-methyl-1H-pyrimidine-2,4-dione；1-(3,5-O-isopropylidene-β-D-2-deoxyxylofuranosyl)thymine；1-[(4aR,6R,7aR)-2,2-dimethyl-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 99018-98-1
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: GMRPGTFTHCYXBX-OPRDCNLKSA-N

物化性质

• 密度：
  1.261±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,5-O-Isopropylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine 以 甲醇 、 丙酮 、 三氟乙酸 为溶剂， 生成 1-(β-D-xylofuranosyl)-thymine
  参考文献：
  名称：

  Process for the deoxygenation of nucleosides

  摘要：

  一种高效的去氧化核苷的过程，包括将羟基与3-卤代丙腈或2-硝基乙基卤代烷基和二硫化碳在碱性条件下反应，形成2'-或3'-(氰基乙硫或硝基乙硫)硫代羰基，然后通过还原消除并用氢取代。这种去氧化过程可用于需要消除2'-或3'-羟基的各种核苷合成，包括制备3'-取代-2',3'-二脱氧核苷，如3'-叠氮-3'-脱氧胸苷和3'-叠氮-2',3'-二脱氧尿苷。

  公开号：

  US05384396A1
• 作为产物：
  描述：

  Phenyl 3,5-di-O-acetyl-2-deoxy-1-thio-α-D-threo-pentofuranoside 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 1.75h， 生成 1-(3,5-O-Isopropylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Stereoselective Synthesis of 2'-Deoxy-.beta.-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases

  摘要：

  The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-alpha-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (alpha:beta = 1:24-0:1) to afford 2'-deoxy-beta-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields. The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable a form. A subsequent S(N)2 type attack to the intermediate will lead to the beta-nucleosides. By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-beta-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside. On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products. The product distribution of the regioisomers was, however, proved to change with reaction time. For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (alpha:beta = 1:2-1:4.8). The isolated yields of the 9-beta isomers after purification were acceptable for practical use.

  DOI：

  10.1021/jo00104a020

文献信息

• Ring Enlargement of Cyclic Acetals and Ketals:  A Way to Seven-Membered Nucleoside Phostones
  作者：Ondřej Páv、Ivan Barvík、Miloš Buděšínský、Milena Masojídková、Ivan Rosenberg

  DOI：10.1021/ol7023899

  日期：2007.12.1

  Novel seven-membered nucleoside phostones were prepared by the reaction of chlorodiethyl phosphite with 3',5'-acetals or ketals derived from xylo-dT. A mechanism for the ring enlargement was proposed, and support for it was provided by ab initio calculations.

  通过亚磷酸氯二乙酯与衍生自xylo-dT的3'，5'-缩醛或缩酮的反应制备了新型的七元核苷磷脂。提出了一种扩大环的机制，并通过从头算来为其提供支持。
• Radiologic Agents for Monitoring Alzheimer's Disease Progression and Evaluating a Response to Therapy and Processes for the Preparation of Such Agents
  申请人：Kortylewicz Zbigniew P.

  公开号：US20090117041A1

  公开（公告）日：2009-05-07

  Disclosed are certain cycloSalingenyl pyrimidine nucleoside monophosphates comprising positron emitters or gamma-emitting radiohalides, uses thereof for monitoring Alzheimer's disease progression and evaluating response to therapy and process for their preparation.

  本文披露了包含正电子发射体或伽马辐射放射性卤化物的某些环丝氨基嘧啶核苷酸单磷酸盐，其用于监测阿尔茨海默病的进展并评估对治疗的反应，以及它们的制备过程。
• Nucleoside 5′-C-phosphonates: reactivity of the α-hydroxyphosphonate moiety
  作者：Šárka Králíková、Miloš Buděšínký、Milena Masojídková、Ivan Rosenberg

  DOI：10.1016/j.tet.2006.03.008

  日期：2006.5

  We found that various dialkyl phosphites, dialkyl trimethylsilyl phosphites, and tris-trimethylsilyl phosphite reacted smoothly with nucleoside 5'-aldehydes to afford epimeric nucleoside 5'-C-phosphonates in high yields. A number of these compounds in both the 2'-deoxyribo and ribo series were prepared. In the case of 2'-deoxythymidine-5'-aldehyde, a thorough study was made on the influence of the 5'-hydroxyl protecting group, type of phosphite, base, and solvent, on the yield and epimeric ratio of the resulting 5'-hydroxyphosphonates. Partial stereoselectivity in favour of either R or S epimers was observed. An attempt to transform the alpha-hydroxyl of the phosphonate moiety into a halo or azido moiety was not Successful. Only intramolecular substitution reaction of the mesyloxy group for an alkoxy residue of the 2-hydroxyethyl ester took place in a low yield. (c) 2006 Elsevier Ltd. All rights reserved.
• β-Selective synthesis of 2'-deoxynucleosides by the coupling of 2-deoxy-1-thio-D-threo-pentofuranosides with silylated thymine
  作者：Hideyuki Sugimura、Keiko Sujino、Kenji Osumi

  DOI：10.1016/s0040-4039(00)92229-9

  日期：1992.4

  The coupling of the 3,5-O-isopropylidene derivative of phenyl 2-deoxy-1-thio-D-threo-pentofuranoside with silylated thymine in the presence of N-bromosuccinimide yielded 1-(2-deoxy-beta-D-threo-pentofuranosyl)thymine with highly anomeric selectivity.
• MEHGURO, XIROMU;ORUJ, JO;FUDZITA, AKIRA
  作者：MEHGURO, XIROMU、ORUJ, JO、FUDZITA, AKIRA

  DOI：——

  日期：——