1447810-31-2

Upstream product

• 1447810-30-1 (1R)-1-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]but-3-en-1-ol 
• 100-39-0 benzyl bromide 
• 28072-61-9 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 

Downstream Products

• 1447810-36-7 C₂₁H₂₃NO₅ 
• 1447810-32-3 (3R)-3-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]-3-(benzyloxy)propanal 
• 1447810-33-4 (3aR,4aS,5R,8aS,8bR)-N-benzyloxycarbonyl-5-(benzyloxy)-2,2-dimethyloctahydro[1,3]dioxolo[4,5]furo[3,2-b]pyridine 
• 1447810-34-5 (2R,3S,4R)-N-benzyloxycarbonyl-4-(benzyloxy)-2-(hydroxymethyl)piperidin-3-ol 
• 1447810-37-8 (2S,3S,4R)-N-benzyloxycarbonyl-4-(benzyloxy)-3-hydroxypiperidine-2-carboxylic acid 
• 1447810-39-0 ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate 

Relevant academic research and scientific papers

Divergent synthesis of 4-epi-fagomine, 3,4-dihydroxypipecolic acid, and a dihydroxyindolizidine and their β-galactosidase inhibitory and immunomodulatory activities

A divergent asymmetric synthesis of the titled iminosugars has been formulated starting from a chiral homoallyl alcohol as the versatile intermediate. The homoallyl alcohol was prepared by a highly diastereoselective Barbier reaction on a d-glucose-derived aldehyde. The protection of its hydroxyl function followed by reductive ozonolysis of the olefin and a subsequent one-pot three-step protocol involving a Staudinger reaction, reductive amination, and benzyloxy carbonyl protection yielded an important bicyclic furanopiperidine derivative. This was converted to the target compounds by following standard reactions. Among the synthesized compounds, 4-epi-fagomine (2b) was the best β-galactosidase inhibitor, and it also prevented LPS-mediated activation of Raw 264.7 macrophage cells. Its congener, 3,4-dihydroxypipecolic acid (4b) also showed similar trends in its cytokine- and enzyme-inhibitory properties at a low concentration (10 μM) but was proinflammatory at higher concentrations. The bicyclic compound dihydroxyindolizidine (21) reduced the proinflammatory cytokine (IL-1β and TNF-α) levels in the LPS-activated Raw 264.7 cells without showing any enzyme-inhibition activity.