Synthesis of 3-Methoxyoxetane δ-Amino Acids with D-lyxo, D-ribo, and D-arabino Configurations

Starting from 1,2-isopropylidene-d-xylose (1), 3-methoxyoxetane δ-amino acids with d-lyxo, d-ribo, and d-arabino configurations were synthesized. The early introduction of an azide function at C-5 of 1 shortened the synthetic pathway. Ring contraction of the intermediate d-xylono-1,4-lactone 6 via t...

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Published in:Journal of carbohydrate chemistry 2008-06, Vol.27 (3), p.172-187
Main Authors: Lucas, Susana Dias, Rauter, Amélia Pilar, Wessel, Hans Peter
Format: Article
Language:English
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Carbohydrate amino acids
Carbohydrate scaffolds
Oxetanes
δ-Amino acids
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description Starting from 1,2-isopropylidene-d-xylose (1), 3-methoxyoxetane δ-amino acids with d-lyxo, d-ribo, and d-arabino configurations were synthesized. The early introduction of an azide function at C-5 of 1 shortened the synthetic pathway. Ring contraction of the intermediate d-xylono-1,4-lactone 6 via triflation and treatment with base led to the corresponding 3-methoxyoxetane δ-amino ester with d-lyxo configuration 7. The analogous procedure for d-ribono-1,4-lactone 16 furnished a mixture of d-ribo and d-arabino esters 17 and 18. Hydrolysis of the methyl esters 7, 17, and 18 to their corresponding δ-amino acids was successful with LiOH in THF, in contrast to that of their 3-hydroxy analog 11.
doi_str_mv 10.1080/07328300802061717
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subjects Carbohydrate amino acids
Carbohydrate scaffolds
Oxetanes
δ-Amino acids
title Synthesis of 3-Methoxyoxetane δ-Amino Acids with D-lyxo, D-ribo, and D-arabino Configurations
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