66048-70-2

Upstream product

• 66048-67-7 5-N-acetylaminomethyl-2-diacetylamino-3,4-dihydro-3-methoxymethyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one 
• 61210-21-7 2-amino-5-cyano-3,4-dihydro-7-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4-one 
• 148495-03-8 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-chloro-5-cyano-4-oxo-3,4-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-tetrahydro-furan-3-yl ester 
• 61210-38-6 5-cyano-2,4-dichloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 103949-67-3 2-acetylamino-5-azidomethyl-6-bromo-3,4-dihydro-3-methoxymethyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one 
• 66048-64-4 6-bromo-2-diacetylamino-3,4-dihydro-3-methoxymethyl-5-methyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one 

Relevant academic research and scientific papers

Synthesis of pyrrolo[2,3-d]pyrimidines that are structurally related to methylated guanosines from tRNA and the nucleoside Q analogs, PreQ0 and PreQ1

The N-3- and N-2-methylated analogs of several 5-substituted 2-amino-7- (β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-ones were synthesized from 5- cyano-2,4-dichloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3- d]pyrimidine (10). These compounds are analogs of nucleoside Q that are methylated in a manner similar to some of the naturally occurring methylated guanosines.

SYNTHESES OF HYPERMODIFIED NUCLEOSIDE Q, AND ITS BIOSYNTHETIC PRECURSORS PREQ0 AND PREQ1

The nucleoside Q (1) and its biosynthetic precursors, preQ0 (2) and preQ1 (3) were synthesized from the key intermediate, 6-bromo-2-diacetylamino-3,4-dihydro-3-methoxymethyl-5-methyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolopyrimidin-4-one (6) by conversion of the methyl group on the base to 3S,4R,5S-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl, cyano, and aminomethyl groups, respectively.