1-(3,5-Di-O-acetyl-2-deoxy-β-D-threo-pentofuranosyl)thymine | 97834-40-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3,5-Di-O-acetyl-2-deoxy-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1,3-Dimethylthymidine；1-(3,5-di-O-acetyl-β-D-threopentofuranosyl)thymine；3',5'-Diacetylthymidine；[(2R,3R,5R)-3-acetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 97834-40-7
• 化学式: C₁₄H₁₈N₂O₇
• 分子量: 326.306
• InChiKey: RGVBNBFNSBMXID-IJLUTSLNSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,5-Di-O-acetyl-2-deoxy-β-D-threo-pentofuranosyl)thymine 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 [(2R,3R,5R)-3-acetyloxy-5-[5-(bromomethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  人5'（3'）-脱氧核糖核苷酸酶的双膦酸盐核苷抑制剂的基于结构的优化

  摘要：

  通过使用基于结构的方法，设计了双膦酸酯核苷衍生物，作为人胞质和线粒体5'-核苷酸酶的有效抑制剂。

  DOI：

  10.1002/ejoc.201800515
• 作为产物：
  描述：

  Phenyl 2-deoxy-1-thio-α-D-threo-pentofuranoside 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 4.33h， 生成 1-(3,5-Di-O-acetyl-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

• 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。
• Structure-based design of a bisphosphonate 5′(3′)-deoxyribonucleotidase inhibitor
  作者：Petr Pachl、Ondřej Šimák、Pavlína Řezáčová、Milan Fábry、Miloš Buděšínský、Ivan Rosenberg、Jiří Brynda

  DOI：10.1039/c5md00235d

  日期：——

  Based on previously known inhibitor–enzyme complex structures, we developed a promising inhibitor by mimicking the phosphate ion and achieved 50- and 100-fold increases in the inhibitory potency towards cdN and mdN, respectively.

  根据先前已知的抑制剂-酶复合物结构，我们通过模拟磷酸根离子开发了一种有前途的抑制剂，并分别在对cdN和mdN的抑制效力上实现了50倍和100倍的增加。
• NOVEL SELENY-METHYLURACIL COMPOUNDS, RADIOSENSITIZER AND PHARMACEUTICAL COMPOSITION USING THEM
  申请人：Hong In Seok

  公开号：US20130211067A1

  公开（公告）日：2013-08-15

  Provided are novel selenyl-methyluracil compounds and a pharmaceutical composition for enhancing the effect of radiation treatment. The composition contains at least one compound selected from the group consisting of the selenyl-methyluracil compounds or pharmaceutically acceptable salts thereof, as an active ingredient.

  提供了一种新的硒基甲基尿嘧啶化合物和一种用于增强放射治疗效果的药物组合物。该组合物包含至少一种从硒基甲基尿嘧啶化合物或其药学上可接受的盐中选择的活性成分。
• METHOD FOR PREPARING DNA FRAGMENT HAVING STICKY END
  申请人：Komiyama Makoto

  公开号：US20110009607A1

  公开（公告）日：2011-01-13

  The present invention provides a method for preparing a DNA fragment, in which a desired double-stranded DNA fragment having a sticky end is directly and easily obtained from an amplification product (an amplified fragment) after PCR without a restriction enzyme digestion. The method for preparing a DNA fragment having a sticky end of the present invention comprises: (i) a step of performing a PCR reaction using a template DNA and specific primers to obtain an amplified DNA fragment; and (ii) a step of performing a prescribed treatment on the amplified DNA fragment to dissociate a protecting group from the fragment. Herein, the above-mentioned specific primers are composed of a complementary DNA portion consisting of a nucleotide sequence complementarily binding to an amplification target region in a template DNA and a non-complementary DNA portion consisting of a nucleotide sequence that links to the 5′ end of the complementary DNA portion but does not complementarily bind to the amplification target sequence, and at least a base corresponding to the 3′ end in the nucleotide sequence of the non-complementary DNA portion is modified with a protecting group capable of terminating the progression of DNA replication catalyzed by a DNA polymerase.

  本发明提供了一种制备DNA片段的方法，其中在PCR后，无需限制性内切酶消化，即可直接轻松地从扩增产物（扩增片段）中获得具有粘性末端的所需双链DNA片段。本发明的制备具有粘性末端的DNA片段的方法包括：（i）使用模板DNA和特异性引物进行PCR反应，以获得扩增的DNA片段；（ii）对扩增的DNA片段进行规定的处理，以使保护基从片段中解离。此处，上述特异性引物由互补DNA部分和非互补DNA部分组成。互补DNA部分包括与模板DNA中扩增目标区域互补配对的核苷酸序列，而非互补DNA部分包括连接到互补DNA部分5'端的核苷酸序列，但不与扩增目标序列互补配对，而且至少有一个与非互补DNA部分核苷酸序列中3'端相对应的碱基被保护基修饰，该保护基能够终止由DNA聚合酶催化的DNA复制的进展。
• 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.