183498-53-5

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 183498-51-3 (1S,2R,3S,5S)-benzoic acid 3-hydroxy-2-hydroxymethyl-5-(thymin-1-yl)-cyclopentylmethyl ester 
• 183498-36-4 (1S,2S,3R,4S)-[4-benzyloxy-3-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl]carbamic acid allyl ester 
• 183498-48-8 (1S,2R,3S,5S)-benzoic acid 3-benzyloxy-2-benzyloxymethyl-5-(thymin-1-yl)-cyclopentylmethyl ester 
• 183498-40-0 (1S,2S,3R,4S)-1-[4-benzyloxy-3-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl]-3-(3-methoxy-2-methyl-acryloyl)-urea 
• 183498-42-2 (1S,2S,3R,4S)-1-(4-benzyloxy-3-benzyloxymethyl-2-hydroxymethyl-cyclopentyl)-thymine 
• 183498-38-6 (1S,2S,3R,4S)-4-benzyloxy-3-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentylamine 
• 132151-65-6 (E)-3-methoxy-2-methylacryloyl isocyanate 

Relevant academic research and scientific papers

6'-Carbon-substituted carbocyclic analogs of 2'-deoxyribonucleosides - Synthesis and effect on DNA/RNA duplex stability

6'-α-Methyl and 6'-α-hydroxymethyl carbocyclic thymidines 11 and 22 have been synthesized via bicyclic lactone 2 and amines 9 and 19, respectively, as key intermediates. Both nucleoside analogs were subsequently elaborated into 5'-O-DMTr protected 3'-phosphoramidites of 6'-α-methyl and 6'-α-hydroxymethyl carbocyclic thymidines as well as appropriately base protected 5-methyl 2'-deoxycytidines. Analysis of the RNA-binding affinity of modified oligodeoxyribonucleotides incorporating these 6'-substituted carbocyclic nucleoside analogs revealed a strongly position dependent effect on DNA/RNA duplex stability. While duplex stability is significantly reduced by point modifications at separated sequence positions, it is only marginally affected by stretches of contiguous modified building blocks.