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

• Published in: Journal of carbohydrate chemistry Vol. 27; no. 3; pp. 172 - 187
• Main Authors: Lucas, Susana Dias, Rauter, Amélia Pilar, Wessel, Hans Peter
• Format: Journal Article
• Language: English
• Published: PHILADELPHIA Taylor & Francis Group 01.06.2008; Taylor & Francis
• Subjects: Biochemistry & Molecular Biology; Carbohydrate amino acids; Carbohydrate scaffolds; Chemistry; Chemistry, Organic; Life Sciences & Biomedicine; Oxetanes; Physical Sciences; Science & Technology; δ-Amino acids; carbohydrate amino acids; REVERSED CYCLONUCLEOSIDE ANALOGS; DESIGN; D-XYLOSE; OXETANE RINGS; RING-CONTRACTION; oxetanes; carbohydrate scaffolds; L-RHAMNOSE; delta-amino acids; ANTIBIOTIC OXETIN; EFFICIENT S(N)2 REACTIONS; SCAFFOLDS
• ISSN: 0732-8303; 1532-2327
• DOI: 10.1080/07328300802061717

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.