195519-97-2

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 195519-95-0 2-(3'-deoxythymidin-3'-yl)-N-((5'S)-5'-deoxy-5'-ethylthymidin-5'-yl)acetamide 
• 195519-88-1 1-[(2R,4S,5R)-5-((S)-1-Amino-allyl)-4-benzyloxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione 
• 195519-93-8 N-{(5'S)-3-O-benzyl-3-[(benzyloxy)methyl]-5'-deoxy-5'-ethenylthymidin-5'-yl}-2-[3'-deoxy-5'-O-(dimethoxytrityl)thymidin-3'-yl]acetamide 
• 195519-91-6 [(2S,3R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester 
• 195519-90-5 [(2S,3R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid 
• 195519-89-2 2-(3'-deoxythymidin-3'-yl)acetic acid 
• 172033-24-8 [(2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid 

Relevant academic research and scientific papers

114. Aza-claisen rearrangement: Synthesis of 5'-branched 5'- aminothymidines

The syntheses of both diastereoisomers of 5'-ethyl-substituted thymidine dimers, the (5'R)- and (5'S)-configurated 33a and 33b, respectively, in which the natural phosphodiester linkage is replaced by an amide group (C(3')- CH2CONH-CH(5')(Et)), are described. Their fully protected derivatives 35a and 35b, respectively, are suitable for incorporation into antisense oligonucleotides. Unexpectedly, an attempted Pd(II)-catalysed aza-Claisen rearrangement of trichloroacetimidate 7 provided the diastereoisomerically pure cyclopropane derivative 17, whose structure was confirmed by X-ray analysis.