903570-48-9

Upstream product

• 1699-59-8 3,4-dibenzyloxybenzyl chloride 
• 50-89-5 thymidine 
• 164267-52-1 5'-O-tert-butyldimethylsilyl-3'-O-(4,4'-dimethoxytriphenylmethyl)thymidine 
• 40733-28-6 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine 
• 903570-39-8 1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione 
• 903570-37-6 1-[4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione 
• 903570-47-8 1-{(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione 
• 903570-49-0 3-(2-Benzenesulfonyl-ethyl)-1-{(2R,4S,5R)-5-(3,4-bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

2-(Phenylthio)ethyl as a novel two-stage base protecting group for thymidine analogues

2-(Phenylthio)ethyl is here proposed for temporary masking the thymine residue in the synthesis of sugar modified thymidine derivatives. This protection has been devised as a 'two-stage' system. The 2-(phenylthio)ethyl residue can be easily and regiospecifically inserted at the N3-position of the pyrimidine by a Mitsunobu reaction with 2-(phenylthio)ethanol and is perfectly stable also to strongly basic conditions. This allowed us to selectively achieve O-alkylation of the ribose moieties in satisfactory yields, avoiding undesired base alkylations. After oxidation of the thioether to sulfone, the thymine protecting group can be totally removed, by a β-elimination mechanism, upon the same basic treatment required for the final deprotection and detachment of oligonucleotides from the support in solid-phase synthesis protocols. Georg Thieme Verlag Stuttgart.