1402155-01-4Relevant academic research and scientific papers
Polyhydroxyamino-piperidine-type iminosugars and pipecolic acid analogues from a D -mannose-derived aldehyde
Matassini, Camilla,Mirabella, Stefania,Ferhati, Xhenti,Faggi, Cristina,Robina, Inmaculada,Goti, Andrea,Moreno-Clavijo, Elena,Moreno-Vargas, Antonio J.,Cardona, Francesca
, p. 5419 - 5432 (2014)
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. The synthesis of diversely substituted polyhydroxypiperidines, polyhydroxyaminopiperidines, and trihydroxypipecolic acid derivatives is reported, using Strecker reactions and double reductive aminations, starting from a D-mannose-derived aldehyde. Copyright
