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

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

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.

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.

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.