219673-08-2

Upstream product

• 1027840-57-8 2-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethanol 
• 190771-53-0 Acetic acid 2-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl ester 
• 190771-50-7 Acetic acid 2-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl ester 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 219673-01-5 5-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine 

Downstream Products

• 219673-07-1 4-chloro-7-(3,5-di-O-p-toluoyl-2-deoxy-β-D-ribofuranosyl)-5-(2-hydroxyethyl)-7H-pyrrolo[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Synthesis of a hydrogen-bond-degenerate tricyclic pyrrolopyrimidine nucleoside and of its 5′-triphosphate

The syntheses of a number of 7-(2-deoxyribofuranosyl)pyrrolo[2,3-d]pyrimidine derivatives are described. Of these the 2-methylsulfanyl-4-hydroxy-5-acetoxyethyl derivative 7 was conveniently formed by condensation of 2-methylsulfanyl-4-hydroxy-6-aminopyrimidine with 2-chloro-4-acetoxybutanal 6; it was then converted to the 4-chloro derivative 12 with phosphoryl trichloride and coupled to 3,5-di-p-toluoyl-2-deoxy-α-ribosyl chloride. Transformation to the 5-aminooxyethyl derivative and ring closure of the latter gave the tricyclic 2-(2-deoxyribosyl)-4-methylsulfonyl-7-oxa-2,3,5,6-tetraazabenz[cd]azulene. Hydrazinolysis of the methylsulfonyl residue, then mercury(II) oxide oxidation, led to the target nucleoside 4. For its study as a polymerase substrate for incorporation into DNA the 5′-triphosphate was synthesised.