224157-49-7

Upstream product

• 224177-27-9 5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane 
• 116264-65-4 ω-tertbutyldimethyl-silyloxyallyltrimethylsilane 
• 146604-43-5 1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil 

Downstream Products

• 927687-31-8 3'-O-tert-butyldiphenylsilyl-5'-C(R)-(2''-hydroxyethyl)thymidine 
• 927687-37-4 C₅₉H₆₅N₄O₁₄PSi 
• 927687-39-6 C₅₉H₆₅N₄O₁₄PSi 
• 927687-35-2 2-cyanoethyl 3'-O-[5'-O-(4'',4'''-dimethoxytrityl)]thymidinyl-5'-C(R)-2''-tosyloxyethyl-3'-(tert-butyldiphenylsilyl)thymidinyl phosphoric ester 
• 927687-33-0 5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine 
• 927687-41-0 C₄₃H₄₇N₄O₁₄P 
• 927687-43-2 C₄₃H₄₇N₄O₁₄P 

Relevant academic research and scientific papers

Stereoselective synthesis of (5′S)-5′-C-(5-bromo-2-penten-1-yl)-2′-deoxyribofuranosyl thymine, a new convertible nucleoside

A stereoselective synthesis of (5′S)-5′-C-(5-bromo-2-penten-1-yl)-2′-deoxyribofuranosyl thymine phosphoramidite is described; the absolute stereochemistry of the compound has been determined by X-ray diffraction analysis. This convertible nucleoside has been incorporated into oligodeoxynucleotides (ODNs) and proved to be suitable for post-synthesis conjugation on solid support. When a diamine is tethered, there is no alteration in the pairing properties of the ODNs. Molecular modelling indicates that the substituent is inserted into the minor groove of the duplex.

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.