Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid
An enantiospecific synthesis of the tetrahydrofuran amino acid (2S,5S)-5-(aminomethyl)-tetrahydrofuran-2-carboxylic acid 1 is reported. The sugar enone 2-(S)-octyl 6-O-acetyl-3,4-dideoxy-α-d-glycero-hex-3- enopyranosid-2-ulose 2a, derived from galactose, was employed as a chiral precursor. The enone...
Guardado en:
| Publicado: |
2010
|
|---|---|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v21_n19_p2435_Uhrig http://hdl.handle.net/20.500.12110/paper_09574166_v21_n19_p2435_Uhrig |
| Aporte de: |
| id |
paper:paper_09574166_v21_n19_p2435_Uhrig |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_09574166_v21_n19_p2435_Uhrig2023-06-08T15:56:30Z Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid 2 propyl 3,4 dideoxy alpha dextro erythro hexopyranoside 5 (aminomethyl)tetrahydrofuran 2 carboxylic acid 5 (azidomethyl) tetrahydrofuran 2 carboxylate 5 (azidomethyl)tetrahydrofuran 2 carboxylic acid 6 azido 2 o tosyl 3,4,6 trideoxy alpha beta dextro erythro hexopyranose 6 azido 2 o tosyl 3,4,6 trideoxy dextro erythro hexono 1,5 lactone aminosugar galactose lactone octyl 2,6 di o tosyl 3,4 dideoxy alpha dextro erythro hexopyranoside octyl 3,4 dideoxy alpha dextro erythro hexopyranoside octyl 6 azido 2 o tosyl 3,4,6 trideoxy alpha dextro erythro hexopyranoside octyl 6 o acetyl 3,4 dideoxy alpha dextro glycero hex 3 enopyranosid 2 ulose octyl 6 o acetyl 3,4 dideoxy alpha dextro glycerohex 3 enopyranosid 2 ulose unclassified drug article chemical reaction kinetics diastereoisomer drug structure drug synthesis hydrolysis methanolysis priority journal proton nuclear magnetic resonance stereochemistry An enantiospecific synthesis of the tetrahydrofuran amino acid (2S,5S)-5-(aminomethyl)-tetrahydrofuran-2-carboxylic acid 1 is reported. The sugar enone 2-(S)-octyl 6-O-acetyl-3,4-dideoxy-α-d-glycero-hex-3- enopyranosid-2-ulose 2a, derived from galactose, was employed as a chiral precursor. The enone 2a was converted by chemical manipulation of the functional groups into the 6-azido-2-O-tosyl-3,4,6-trideoxy-d-erythro-hexono-1,5-lactone 9 as key intermediate. Methanolysis of 9 induced the opening of the lactone and the attack of the hydroxyl group at C-5 to C-2 with the displacement of the tosylate. This reaction led to the formation of the tetrahydrofuran ring of methyl (2S,5S)-5-(azidomethyl)-tetrahydrofuran-2-carboxylate 10, which was readily converted into 1. The overall yield of the sequence was 35%, and all the intermediates and the final product have been fully characterized. In addition, the preferential conformations in solution of lactone 9 and target molecule 1 have been established. © 2010 Elsevier Ltd. All rights reserved. 2010 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v21_n19_p2435_Uhrig http://hdl.handle.net/20.500.12110/paper_09574166_v21_n19_p2435_Uhrig |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
2 propyl 3,4 dideoxy alpha dextro erythro hexopyranoside 5 (aminomethyl)tetrahydrofuran 2 carboxylic acid 5 (azidomethyl) tetrahydrofuran 2 carboxylate 5 (azidomethyl)tetrahydrofuran 2 carboxylic acid 6 azido 2 o tosyl 3,4,6 trideoxy alpha beta dextro erythro hexopyranose 6 azido 2 o tosyl 3,4,6 trideoxy dextro erythro hexono 1,5 lactone aminosugar galactose lactone octyl 2,6 di o tosyl 3,4 dideoxy alpha dextro erythro hexopyranoside octyl 3,4 dideoxy alpha dextro erythro hexopyranoside octyl 6 azido 2 o tosyl 3,4,6 trideoxy alpha dextro erythro hexopyranoside octyl 6 o acetyl 3,4 dideoxy alpha dextro glycero hex 3 enopyranosid 2 ulose octyl 6 o acetyl 3,4 dideoxy alpha dextro glycerohex 3 enopyranosid 2 ulose unclassified drug article chemical reaction kinetics diastereoisomer drug structure drug synthesis hydrolysis methanolysis priority journal proton nuclear magnetic resonance stereochemistry |
| spellingShingle |
2 propyl 3,4 dideoxy alpha dextro erythro hexopyranoside 5 (aminomethyl)tetrahydrofuran 2 carboxylic acid 5 (azidomethyl) tetrahydrofuran 2 carboxylate 5 (azidomethyl)tetrahydrofuran 2 carboxylic acid 6 azido 2 o tosyl 3,4,6 trideoxy alpha beta dextro erythro hexopyranose 6 azido 2 o tosyl 3,4,6 trideoxy dextro erythro hexono 1,5 lactone aminosugar galactose lactone octyl 2,6 di o tosyl 3,4 dideoxy alpha dextro erythro hexopyranoside octyl 3,4 dideoxy alpha dextro erythro hexopyranoside octyl 6 azido 2 o tosyl 3,4,6 trideoxy alpha dextro erythro hexopyranoside octyl 6 o acetyl 3,4 dideoxy alpha dextro glycero hex 3 enopyranosid 2 ulose octyl 6 o acetyl 3,4 dideoxy alpha dextro glycerohex 3 enopyranosid 2 ulose unclassified drug article chemical reaction kinetics diastereoisomer drug structure drug synthesis hydrolysis methanolysis priority journal proton nuclear magnetic resonance stereochemistry Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid |
| topic_facet |
2 propyl 3,4 dideoxy alpha dextro erythro hexopyranoside 5 (aminomethyl)tetrahydrofuran 2 carboxylic acid 5 (azidomethyl) tetrahydrofuran 2 carboxylate 5 (azidomethyl)tetrahydrofuran 2 carboxylic acid 6 azido 2 o tosyl 3,4,6 trideoxy alpha beta dextro erythro hexopyranose 6 azido 2 o tosyl 3,4,6 trideoxy dextro erythro hexono 1,5 lactone aminosugar galactose lactone octyl 2,6 di o tosyl 3,4 dideoxy alpha dextro erythro hexopyranoside octyl 3,4 dideoxy alpha dextro erythro hexopyranoside octyl 6 azido 2 o tosyl 3,4,6 trideoxy alpha dextro erythro hexopyranoside octyl 6 o acetyl 3,4 dideoxy alpha dextro glycero hex 3 enopyranosid 2 ulose octyl 6 o acetyl 3,4 dideoxy alpha dextro glycerohex 3 enopyranosid 2 ulose unclassified drug article chemical reaction kinetics diastereoisomer drug structure drug synthesis hydrolysis methanolysis priority journal proton nuclear magnetic resonance stereochemistry |
| description |
An enantiospecific synthesis of the tetrahydrofuran amino acid (2S,5S)-5-(aminomethyl)-tetrahydrofuran-2-carboxylic acid 1 is reported. The sugar enone 2-(S)-octyl 6-O-acetyl-3,4-dideoxy-α-d-glycero-hex-3- enopyranosid-2-ulose 2a, derived from galactose, was employed as a chiral precursor. The enone 2a was converted by chemical manipulation of the functional groups into the 6-azido-2-O-tosyl-3,4,6-trideoxy-d-erythro-hexono-1,5-lactone 9 as key intermediate. Methanolysis of 9 induced the opening of the lactone and the attack of the hydroxyl group at C-5 to C-2 with the displacement of the tosylate. This reaction led to the formation of the tetrahydrofuran ring of methyl (2S,5S)-5-(azidomethyl)-tetrahydrofuran-2-carboxylate 10, which was readily converted into 1. The overall yield of the sequence was 35%, and all the intermediates and the final product have been fully characterized. In addition, the preferential conformations in solution of lactone 9 and target molecule 1 have been established. © 2010 Elsevier Ltd. All rights reserved. |
| title |
Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid |
| title_short |
Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid |
| title_full |
Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid |
| title_fullStr |
Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid |
| title_full_unstemmed |
Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid |
| title_sort |
enantiospecific synthesis of the sugar amino acid (2s,5s)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid |
| publishDate |
2010 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v21_n19_p2435_Uhrig http://hdl.handle.net/20.500.12110/paper_09574166_v21_n19_p2435_Uhrig |
| _version_ |
1768543381588279296 |