224157-41-9

Upstream product

• 146604-43-5 1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil 
• 244035-21-0 5'(S)-C-allyl-3'-O-(tert-butyldiphenylsilyl)thymidine 
• 224157-40-8 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine 

Downstream Products

• 224157-42-0 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(oxo-propan)-thymidine 
• 224157-43-1 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(hex-3-ene-1-ol)-thymidine 
• 1360614-03-4 C₃₉H₄₉N₄O₁₁PSi 
• 1360614-04-5 C₃₉H₄₉N₄O₁₁PSi 
• 1360613-98-4 (5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)-5'-O-(trimethylsilyl)thymidine 
• 1360613-99-5 (5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)thymidine 
• 1360614-00-1 ethyl [(5'S)-5'-C-(3-bromopropyl)-3'-O-(tert-butyldiphenylsilyloxy)thymidine-5'-O-yl][(5'-O-dimethoxytrityl)thymidine-3'O-yl]phosphite 

Relevant academic research and scientific papers

Synthesis of phostone-constrained nucleic acid (P-CNA) dinucleotides through intramolecular Arbuzov's reaction

P-CNAs are dinucleotide building blocks in which the torsional angles α and β of the sugar/phosphate backbone are constrained to non-canonical values within a cyclic phosphonate structure (phostone) synthesised by diastereoselective intramolecular Arbuzov reaction. The reaction has been improved through the use of microwave activation and addition of lithium bromide.

Allylsilanes in the preparation of 5'-C-hydroxy or bromo alkylthymidines

The reaction of 5'-C-thymidine aldehyde with allytrimethylsilane promoted by BF3:Et2O lead stereoselectively to 5'-C(S)-allylthymidine which is converted to 5'-C(S)-hydroxyhexylthymidine. 5'-C-(R or S) hydroxypentylthymidine can be obtained by using ω- tertButyldimethylsilyloxyallyltrimethylsilane in the Sakurai reaction. In the same conditions, ω-Bromoallyltrimethylsilane adds to the aldehyde with a complete transposition of the siliranium intermediate and allows the preparation of the 5'-C(S)-bromopentene derivative.

5'-C-tosyloxyalkylnucleosides. Models for oligonucleotide coupling with nucleophiles

5'-C-substituted nucleosides with an hydroxyalkyl chain are synthesized. The stereochemistry of the new stereogenic center is defined. After introduction of a tosyl group, dimer models are prepared to evaluate the conjugation with amines used as nucleophiles.