Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers
High yielding routes for the synthesis of selectively protected derivatives of D- and L-galactonic acids, having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono-1,4-lactones was developed...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_09574166_v14_n17_p2579_RomeroZaliz |
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todo:paper_09574166_v14_n17_p2579_RomeroZaliz2023-10-03T15:52:23Z Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers Romero Zaliz, C.L. Varela, O. 6 amino 6 deoxy 2,3,4,5 tetra o methyl dextro galactonic acid 6 amino 6 deoxy 2,3,4,5 tetra o methyl levo galactonic acid 6 azido 6 deoxy levo galactono 1,4 lactone acid azide bromine dimethyl sulfoxide ester ester derivative galactose lactone derivative levo galactonolactone methyl 6 azido 6 deoxy 2,3,4,5 tetra o methyl levo galactonate methyl group methyl iodide polymer potassium sodium hydroxide unclassified drug article bromination chemical analysis chemical structure methylation precursor priority journal reaction analysis structure analysis synthesis technique High yielding routes for the synthesis of selectively protected derivatives of D- and L-galactonic acids, having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono-1,4-lactones was developed as a key step of the sequence. For example, 6-azido-6-deoxy-L-galactono-1,4-lactone 16 was converted into the potassium salt and methylated (NaH, DMSO, MeI) to the methyl ester of the 2,3,4,5-tetra-O-methyl derivative 12. Compound 16 was readily prepared by bromination at C-6 of L-galactonolactone 1 and isopropylidenation; followed by substitution of bromine by azide and removal of the protecting groups. Hydrolysis of the methyl ester of 12 and hydrogenation of the azide led to the tetra-O-methyl derivative of the 6-amino acid 18 with 52% overall yield from 1. The same sequence applied to D-galactonolactone 19 led to the enantiomeric amino acid 25 with a 47% overall yield. © 2003 Elsevier Ltd. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09574166_v14_n17_p2579_RomeroZaliz |
| institution |
Universidad de Buenos Aires |
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I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
6 amino 6 deoxy 2,3,4,5 tetra o methyl dextro galactonic acid 6 amino 6 deoxy 2,3,4,5 tetra o methyl levo galactonic acid 6 azido 6 deoxy levo galactono 1,4 lactone acid azide bromine dimethyl sulfoxide ester ester derivative galactose lactone derivative levo galactonolactone methyl 6 azido 6 deoxy 2,3,4,5 tetra o methyl levo galactonate methyl group methyl iodide polymer potassium sodium hydroxide unclassified drug article bromination chemical analysis chemical structure methylation precursor priority journal reaction analysis structure analysis synthesis technique |
| spellingShingle |
6 amino 6 deoxy 2,3,4,5 tetra o methyl dextro galactonic acid 6 amino 6 deoxy 2,3,4,5 tetra o methyl levo galactonic acid 6 azido 6 deoxy levo galactono 1,4 lactone acid azide bromine dimethyl sulfoxide ester ester derivative galactose lactone derivative levo galactonolactone methyl 6 azido 6 deoxy 2,3,4,5 tetra o methyl levo galactonate methyl group methyl iodide polymer potassium sodium hydroxide unclassified drug article bromination chemical analysis chemical structure methylation precursor priority journal reaction analysis structure analysis synthesis technique Romero Zaliz, C.L. Varela, O. Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers |
| topic_facet |
6 amino 6 deoxy 2,3,4,5 tetra o methyl dextro galactonic acid 6 amino 6 deoxy 2,3,4,5 tetra o methyl levo galactonic acid 6 azido 6 deoxy levo galactono 1,4 lactone acid azide bromine dimethyl sulfoxide ester ester derivative galactose lactone derivative levo galactonolactone methyl 6 azido 6 deoxy 2,3,4,5 tetra o methyl levo galactonate methyl group methyl iodide polymer potassium sodium hydroxide unclassified drug article bromination chemical analysis chemical structure methylation precursor priority journal reaction analysis structure analysis synthesis technique |
| description |
High yielding routes for the synthesis of selectively protected derivatives of D- and L-galactonic acids, having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono-1,4-lactones was developed as a key step of the sequence. For example, 6-azido-6-deoxy-L-galactono-1,4-lactone 16 was converted into the potassium salt and methylated (NaH, DMSO, MeI) to the methyl ester of the 2,3,4,5-tetra-O-methyl derivative 12. Compound 16 was readily prepared by bromination at C-6 of L-galactonolactone 1 and isopropylidenation; followed by substitution of bromine by azide and removal of the protecting groups. Hydrolysis of the methyl ester of 12 and hydrogenation of the azide led to the tetra-O-methyl derivative of the 6-amino acid 18 with 52% overall yield from 1. The same sequence applied to D-galactonolactone 19 led to the enantiomeric amino acid 25 with a 47% overall yield. © 2003 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Romero Zaliz, C.L. Varela, O. |
| author_facet |
Romero Zaliz, C.L. Varela, O. |
| author_sort |
Romero Zaliz, C.L. |
| title |
Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers |
| title_short |
Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers |
| title_full |
Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers |
| title_fullStr |
Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers |
| title_full_unstemmed |
Straightforward synthesis of derivatives of D- and L-galactonic acids as precursors of stereoregular polymers |
| title_sort |
straightforward synthesis of derivatives of d- and l-galactonic acids as precursors of stereoregular polymers |
| url |
http://hdl.handle.net/20.500.12110/paper_09574166_v14_n17_p2579_RomeroZaliz |
| work_keys_str_mv |
AT romerozalizcl straightforwardsynthesisofderivativesofdandlgalactonicacidsasprecursorsofstereoregularpolymers AT varelao straightforwardsynthesisofderivativesofdandlgalactonicacidsasprecursorsofstereoregularpolymers |
| _version_ |
1782024026051313664 |