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- Title
Polyhydroxyamino-Piperidine-Type Iminosugars and Pipecolic Acid Analogues from a D-Mannose-Derived Aldehyde.
- Authors
Matassini, Camilla; Mirabella, Stefania; Ferhati, Xhenti; Faggi, Cristina; Robina, Inmaculada; Goti, Andrea; Moreno‐Clavijo, Elena; Moreno‐Vargas, Antonio J.; Cardona, Francesca
- Abstract
A general strategy for the synthesis of diversely substituted 3,4,5-trihydroxypiperidines (including two natural products), 5-amino-3,4-dihydroxypiperidines, 3,4,5-trihydroxypipecolic acids, and 2-(aminomethyl)-3,4,5-trihydroxypiperidines is reported. The procedure used a double reductive amination or a Strecker reaction, starting from differently protected aldehydes readily synthesized on a gram scale from D-mannose. The biological activities of the target compounds were evaluated, and some of them showed moderate inhibition of α- L-fucosidase and β-glucosidase.
- Subjects
NATURAL products; ACID research; AMINATION; ALDEHYDES; MANNOSE
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 25, p5419
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201402427