Synthesis of γ-Hydroxyalkyl Substituted Piperidine Iminosugars from d-Glucose

d-Glucose was converted to synthetic equivalent of meso-pentodialdose, namely 3-C-(1‘-aminoethyl)-α-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 hydrol...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2008-04, Vol.73 (8), p.3284-3287
Main Authors: Mane, Rajendra S., Kumar, K. S. Ajish, Dhavale, Dilip D.
Format: Article
Language:English
Subjects:
Alkylation
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Glucose - chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydroxylation
Imino Sugars - chemical synthesis
Imino Sugars - chemistry
Molecular Structure
Organic chemistry
Piperidines - chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:d-Glucose was converted to synthetic equivalent of meso-pentodialdose, namely 3-C-(1‘-aminoethyl)-α-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 γ-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 γ-hydroxymethyl piperidine iminosugar 4.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800044r