Synthesis of gamma-hydroxyalkyl substituted piperidine iminosugars from D-glucose.
D-Glucose was converted to synthetic equivalent of meso-pentodialdose, namely 3-C-(1'-aminoethyl)-alpha-d-ribo-pentodialdo-1,4-furanose 10 that gives an easy access to manipulate the aldehyde functionalities on either sides to get enantiomeric pair of 3. Thus, reduction of C5-aldehyde followed by hydrolysis of 1,2-acetonide functionality and reductive aminocyclization with C1-aldehyde afforded gamma-1,2-dihydroxyethyl piperidine iminosugar 3. On the other hand, first reductive aminocyclization with C5-aldehyde gave piperidine ring skeleton 12 that on removal of 1,2-acetonide and reduction of C1-aldehyde gave ent-3 while chopping of C1-aldehyde in 12 and reduction afforded gamma-hydroxymethyl piperidine iminosugar 4.
Mane
Rajendra S
RS
Department of Chemistry, Garware Research Centre, University of Pune, Pune- 411 007, India.
Kumar
K S Ajish
KS
Dhavale
Dilip D
DD
D000478:Alkylation; D005947:Glucose / Q000737:chemistry*; D006900:Hydroxylation; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*
D050111:Imino Sugars; D010880:Piperidines; C032727:piperidine; D005947:Glucose