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Synthesis of 3-Methoxyoxetane δ-Amino Acids with D-lyxo, D-ribo, and D-arabino Configurations
Titel:
Synthesis of 3-Methoxyoxetane δ-Amino Acids with D-lyxo, D-ribo, and D-arabino Configurations
Auteur:
Lucas, Susana Dias Rauter, Amelia Pilar Wessel, Hans Peter
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 27 (2008) nr. 3 pagina's 172-187
Jaar:
2008-03
Inhoud:
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.
Uitgever:
Taylor & Francis
Bronbestand:
Elektronische Wetenschappelijke Tijdschriften
Details van artikel 193 van 252 gevonden artikelen