Synthetic reactions of aldonolactones

This chapter examines the synthetic reactions of aldonolactones. Aldonolactones are useful starting materials for the synthesis of modified sugars. They have also been used as chiral templates in the synthesis of natural products. The hydroxyl groups of aldonolactones react with a variety of aldehyd...

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Autores principales: De Lederkremer, R.M., Varela, O.
Formato: SER
Materias:
carbohydrate derivative
carbohydrate synthesis
drug synthesis
priority journal
reaction analysis
review
stereochemistry
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00652318_v50_nC_p125_DeLederkremer
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00652318_v50_nC_p125_DeLederkremer
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spelling todo:paper_00652318_v50_nC_p125_DeLederkremer2023-10-03T14:52:48Z Synthetic reactions of aldonolactones De Lederkremer, R.M. Varela, O. carbohydrate derivative carbohydrate synthesis drug synthesis priority journal reaction analysis review stereochemistry This chapter examines the synthetic reactions of aldonolactones. Aldonolactones are useful starting materials for the synthesis of modified sugars. They have also been used as chiral templates in the synthesis of natural products. The hydroxyl groups of aldonolactones react with a variety of aldehydes and ketones to give the corresponding acetal derivatives. D-Ribono-1,4-lactone readily condenses with acetone, under acidic catalysis with mineral acids or anhydrous copper sulfate, to give 2,3-O-isopropylidene-D-ribono-1,4-lactone that was employed for the synthesis of 5-deoxy and 5-O-substituted derivatives of D-ribono-1,4 lactone. The reaction of aldonolactones with hydrogen bromide in acetic acid has been extensively studied. The treatment of D-galactono-1,4-lactone with HBr–AcOH for a few hours at room temperature followed by acetylation gave the acetylated 6-bromo-6-deoxy derivative in good yield. The addition of organometallic reagents to the carbonyl group of conveniently substituted aldonolactones constitutes a viable chain-extension method. It is found that the reaction leads to the formation of hemiacetals of glyculoses, 1-methylene sugars, and C-glycosyl compounds, which are precursors of, or occur as subunits of, a variety of natural products. © 1994, Academic Press Inc. Fil:De Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. SER info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00652318_v50_nC_p125_DeLederkremer
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic carbohydrate derivative
carbohydrate synthesis
drug synthesis
priority journal
reaction analysis
review
stereochemistry
spellingShingle carbohydrate derivative
carbohydrate synthesis
drug synthesis
priority journal
reaction analysis
review
stereochemistry
De Lederkremer, R.M.
Varela, O.
Synthetic reactions of aldonolactones
topic_facet carbohydrate derivative
carbohydrate synthesis
drug synthesis
priority journal
reaction analysis
review
stereochemistry
description This chapter examines the synthetic reactions of aldonolactones. Aldonolactones are useful starting materials for the synthesis of modified sugars. They have also been used as chiral templates in the synthesis of natural products. The hydroxyl groups of aldonolactones react with a variety of aldehydes and ketones to give the corresponding acetal derivatives. D-Ribono-1,4-lactone readily condenses with acetone, under acidic catalysis with mineral acids or anhydrous copper sulfate, to give 2,3-O-isopropylidene-D-ribono-1,4-lactone that was employed for the synthesis of 5-deoxy and 5-O-substituted derivatives of D-ribono-1,4 lactone. The reaction of aldonolactones with hydrogen bromide in acetic acid has been extensively studied. The treatment of D-galactono-1,4-lactone with HBr–AcOH for a few hours at room temperature followed by acetylation gave the acetylated 6-bromo-6-deoxy derivative in good yield. The addition of organometallic reagents to the carbonyl group of conveniently substituted aldonolactones constitutes a viable chain-extension method. It is found that the reaction leads to the formation of hemiacetals of glyculoses, 1-methylene sugars, and C-glycosyl compounds, which are precursors of, or occur as subunits of, a variety of natural products. © 1994, Academic Press Inc.
format SER
author De Lederkremer, R.M.
Varela, O.
author_facet De Lederkremer, R.M.
Varela, O.
author_sort De Lederkremer, R.M.
title Synthetic reactions of aldonolactones
title_short Synthetic reactions of aldonolactones
title_full Synthetic reactions of aldonolactones
title_fullStr Synthetic reactions of aldonolactones
title_full_unstemmed Synthetic reactions of aldonolactones
title_sort synthetic reactions of aldonolactones
url http://hdl.handle.net/20.500.12110/paper_00652318_v50_nC_p125_DeLederkremer
work_keys_str_mv AT delederkremerrm syntheticreactionsofaldonolactones
AT varelao syntheticreactionsofaldonolactones
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