3'-O-(tert-butyldimethylsilyl)-5'-(p-toluenesulfonyl)thymidine | 129801-99-6

• 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: 3'-O-(tert-butyldimethylsilyl)-5'-(p-toluenesulfonyl)thymidine
• 英文别名: 5'-O-p-toluenesulfonyl-3'-O-t-butyldimethylsilylthymidine；3'-O-(tert-butyldimethylsilyl)-5'-O-(p-toluenesulfonyl)thymidine；5'-O-p-tosyl-3'-O-(tert-butyldimethylsilyl)thymidine；((2R,3S,5R)-3-((tert-butyldimethylsilyl)oxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate；TBDMS(-3)[Tos(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl；[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 129801-99-6
• 化学式: C₂₃H₃₄N₂O₇SSi
• 分子量: 510.684
• InChiKey: BFJGZBBACRAFGT-XUVXKRRUSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-O-(tert-butyldimethylsilyl)-5'-(p-toluenesulfonyl)thymidine 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 5-O-(4-甲基苯基磺酰基)胸腺嘧啶脱氧核苷
  参考文献：
  名称：

  Synthesis of nucleotide 5'-diphosphates from 5'-O-tosyl nucleosides

  摘要：

  DOI：

  10.1021/jo00385a026
• 作为产物：
  描述：

  对甲苯磺酰氯 在 吡啶 、 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 3'-O-(tert-butyldimethylsilyl)-5'-(p-toluenesulfonyl)thymidine
  参考文献：
  名称：

  采用固相合成来获得抑制 DNA 修复核酸酶 SNM1A 的含胸腺嘧啶核苷类似物

  摘要：

  核苷类似物显示出有用的生物活性特性。提出了一种通用的固相合成方法，可以轻松实现含胸腺嘧啶核苷类似物的多样化。该方法的实用性通过制备用于 SNM1A 分析的化合物库来证明，SNM1A 是一种有助于细胞毒性的 DNA 损伤修复酶。这项探索提供了迄今为止最有前途的 SNM1A 核苷衍生抑制剂，IC 50为 12.3 μM。

  DOI：

  10.1039/d3ob00836c

文献信息

• Introduction of an alkyl group into the sugar portion of uracilnucleosides by the use of Gilman reagents.
  作者：Hiroyuki HAYAKAWA、Hiroshi ASHIZAWA、Hiromichi TANAKA、Tadashi MIYASAKA

  DOI：10.1248/cpb.38.355

  日期：——

  Substitution of a p-toluenesulfonyloxy group in the sugar portion of uracilnucleosides by an alkyl group was investigated by using Gilman reagents (R2CuLi). In the cases of 5'-O-tosyl derivatives of 2', 3'-O-isopropylideneuridine, moderate vields of 5'-alkylated products were obtained. In contrast to this, the reactions of the corresponding 2'-deoxyuridine derivatives gave higher yields of products. A similar substitution reaction at the 3'-position of 2'-deoxyuridine derivatives was also examined.

  用Gilman试剂（R2CuLi）研究了尿嘧啶核苷糖部分的p-甲苯磺酰氧基被烷基取代的反应。对于2',3'-O-异亚丙基尿苷的5'-O-甲苯磺酸衍生物，得到了中等收率的5'-烷基化产物。与此相反，相应的2'-脱氧尿苷衍生物的反应则得到了更高收率的产物。还考察了在2'-脱氧尿苷衍生物的3'位进行类似取代反应的情况。
• Uridine 5′-monoselenoacetals as substrates for diastereoselective homolytic C-C bond formation
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Shigeru Saito、Satomi Kinoshima、Motoi Hosoe、Kazuhiro Kanmuri、Kentaro Yamaguchi、Tadashi Miyasaka

  DOI：10.1016/0040-4020(96)00483-8

  日期：1996.7

  Uridine 5′-monoselenoacetals prepared by the seleno-Pummerer reaction of 5′-deoxy-5′-phenylseleno-uridines were used as substrates for radical-mediated reactions with allyltributyltin. The reaction of the 2′,3′-O-isopropylidene derivative gave cyclized products, 5-allyl-6,5′-cyclonucleosides, whereas those of the 2′,3′-bis-O-(tertbutyldimethylsilyl derivatives underwent the C-C bond formation at the

  通过5'-脱氧-5'-苯基硒代尿苷的硒化-Pummerer反应制备的尿苷5'-单硒缩醛用作与烯丙基三丁基锡进行自由基介导的反应的底物。2'，3'-O-异亚丙基衍生物的反应生成环化产物5-烯丙基-6,5'-环核苷，而2'，3'-双-O-（叔丁基二甲基甲硅烷基衍生物的那些则经历了CC键在5'-位形成（5'S）-和（5'R）-异构体，讨论了两种反应的立体化学结果，还研究了烯丙基三丁基锡以外的自由基受体的使用。
• SYNTHESIS OF SELENIUM-DERIVATIZED NUCLEOSIDES AND OLIGONUCLEOTIDES FOR X-RAY CRYSTALLOGRAPHY
  作者：Nicolas Carrasco、Dov Ginsburg、Quan Du、Zhen Huang

  DOI：10.1081/ncn-100105907

  日期：2001.9.30

  We report here the synthesis of nucleoside and oligonucleotide analogs containing selenium, which serves as an anomalous scattering center to enable MAD phase determination in nucleotide X-ray crystallography. We have developed a phase transfer approach to introduce the selenium functionality in A, C, G, T, and U nucleosides at 5′-positions. In the incorporation of the selenium functionality, the leaving

  我们在这里报告了含有硒的核苷和寡核苷酸类似物的合成，硒作为异常散射中心，可以在核苷酸 X 射线晶体学中确定 MAD 相。我们开发了一种相转移方法，以在 A、C、G、T 和 U 核苷的 5' 位引入硒功能。在引入硒官能团时，离去基团（溴化物、甲磺酰基和甲苯磺酰基）很容易被硒化钠、二硒化钠和甲基硒化钠取代，产率高于 90%。硒衍生的寡核苷酸已通过亚磷酰胺化学合成。
• Oligodeoxynucleotides with extended zwitter-ionic internucleotide linkage
  作者：Svetlana V Kochetkova、Edward N Timofeev、Ekaterina A Korobeinikova、Natalia A Kolganova、Vladimir L Florentiev

  DOI：10.1016/s0040-4020(01)01034-1

  日期：2001.12

  Two non-natural nucleoside analogues, N-(2-hydroxyethyl)-2',5'-dideoxy-5'-aminothymidine (dT(NH)) and N-(2-hydroxyethyl)N-methyl-2,5'-dideoxy-5'-aminothymidine (dT(NMe)), have been prepared and used in the synthesis of oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides, modified at internucleotide linkages. Both modified oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides have been shown to form zwitter-ionic phosphate-amine pairs as evidenced by their decreased electrophoretic mobility in denaturing polyacrylamide gel. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and RNA Binding Selectivity of Oligonucleotides Modified with Five-Atom Thioacetamido Nucleic Acid Backbone Structures
  作者：Khirud Gogoi、Anita D. Gunjal、Usha D. Phalgune、Vaijayanti A. Kumar

  DOI：10.1021/ol070990u

  日期：2007.7.1

  Convenient chemical synthesis and incorporation of dithymidine and thymidine-cytidine dimer blocks connected with a five-atom amide linker N3'-CO-CH2-S-CH2 into oligonucleotides (ONs) are reported. The UV-T-m experiments for binding affinities of these mixed backbone ONs with complementary DNA and RNA sequences revealed important results such as significantly higher RNA-binding selectivity as compared with complementary DNA. NMR studies of the dimer blocks suggested a marginal increase in the N-type sugar conformations over that of the native DNA.