Polyhydroxyamino‐Piperidine‐Type Iminosugars and Pipecolic Acid Analogues from a D‐Mannose‐Derived Aldehyde1. Issue 25 (27th May 2014)

• Record Type: Journal Article
• Authors: Matassini, Camilla; Mirabella, Stefania; Ferhati, Xhenti; Faggi, Cristina; Robina, Inmaculada; Goti, Andrea; Moreno‐Clavijo, Elena; Moreno‐Vargas, Antonio J.; Cardona, Francesca
• Is Part Of: European journal of inorganic chemistry. Issue 25(2014)
• Page Start: 5419
• Page End: 5432
• Publication Date: 2014-05-27
• Subjects: Nitrogen heterocycles -- Alkaloids -- Carbohydrates -- Amination -- Glycomimetics -- Biological activity; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejoc.201402427
• Languages: English
• ISSNs: 1434-1948

Abstract

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 fromD ‐mannose. The biological activities of the target compounds were evaluated, and some of them showed moderate inhibition of α‐L ‐fucosidase and β‐glucosidase. Abstract : The synthesis of diversely substituted polyhydroxypiperidines, polyhydroxyaminopiperidines, and trihydroxypipecolic acid derivatives is reported, using Strecker reactions and double reductive aminations, starting from aD ‐mannose‐derived aldehyde.