An Efficient and Short Route for the Synthesis of Reverse Pyrrole Ribonucleosides
The synthesis of reverse pyrrole ribonucleosides methyl 5-C-(4-acetyl-5-methyl-pyrrol-1-yl)-2,3-O-isopropylidene-5-deoxy- beta-D-ribofuranoside (10), methyl 5-C-(4-ethoxycarbonyl-5-methyl-pyrrol-1-yl)-2,3-O-isopropylidene-5-deoxy- beta-D-ribofuranoside (11), methyl 5-C-(4-acetyl-5-methyl-pyrrol-1-yl)-5-deoxy-beta-D-ribofuranoside (12), methyl 5-C-(4-ethoxycarbonyl-5-methyl-pyrrol-1-yl)-5-deoxy- beta-D-ribofuranoside (13), methyl 5-deoxy-5-C-(3'-formyl-4'-hydroxypropyl-pyrrol-1'-yl)-2,3-O-isopropylidene- beta-D-ribofuranoside (16) and methyl 5-deoxy-5-C-(3'-formyl-pyrrol-1'-yl)-2,3-O-isopropylidene- beta-D-ribofuranoside (18) are described starting from readily available methyl 5-amino-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside (9). The synthetic strategy for the construction of the heterocyclic ring was based on the nucleophilic attack of (9) to 4-acetyl-2-n-butoxy-5-methyl-4,5-dihydrofuran (4), 4-carbetoxy-2-n-butoxy-5-methyl-4,5-dihydrofuran (5), 4-formyl-2-n-butoxy-4,5-dihydrofuran (6) and 4-formyl-1-methyl dioxabyciclo[3.3.0]oct-3-en (8, in situ). The later compounds were obtained from reaction between 3-diazo-2,4-pentadione (1), ethyl 2-diazoacetoacetate (2) or diazomalonaldehyde (3) and enol ethers using dirhodium tetraacetate as a catalyst.
Main Authors: | Pereira,Letícia O. R., Cunha,Anna C., Souza,Maria Cecília B. V. de, Ferreira,Vitor F. |
---|---|
Format: | Digital revista |
Language: | English |
Published: |
Sociedade Brasileira de Química
2002
|
Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000300012 |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
Similar Items
-
Synthesis, Characterization and Antimicrobial Activity of New Pyrrole Derivatives
by: Idhayadhulla,Akbar, et al.
Published: (2011) -
THE APPLICATION OF IRON (III) PHOSPHATE IN THE SYNTHESIS OF N-SUBSTITUTED PYRROLES
by: SAMADI,MARJAN, et al.
Published: (2015) -
Synthesis and anti-breast cancer activity of tetrasubstituted pyrrole derivatives
by: Padrón, José M., et al.
Published: (2005-11) -
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes
by: Ferreira,Cláudio S., et al.
Published: (2010) -
Klein’s Remdesivir-Nucleobase Synthesis Revisited: Chemoselective Cyanation of Pyrrol-2-carboxaldehyde
by: Santos,Juliana A. dos, et al.
Published: (2021)