886852-63-7

Upstream product

• 691870-87-8 4-(tert-butyldimethylsilyloxy)-1-(furan-2-yl)butan-1-one 
• 120853-04-5 1-(furan-2-yl)-4-hydroxybutan-1-one 
• 886852-59-1 (2S,6R)-6-(benzyloxy)-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one 
• 886852-57-9 (S)-1-(furan-2-yl)-4-tert-butyldimethylsilyloxybutan-1-ol 
• 886852-56-8 (2S)-6-hydroxy-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one 
• 886852-62-6 3-((2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2H-pyran-2-yl)propan-1-ol 
• 124-63-0 methanesulfonyl chloride 
• 886852-61-5 (2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-yl methyl carbonate 
• 886852-55-7 (2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran 
• 886852-60-4 (2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-ol 

Downstream Products

• 886852-54-6 3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate 
• 164907-52-2 L-swainsonine 

Relevant academic research and scientific papers

De novo asymmetric synthesis of D- and L-swainsonine

The enantioselective syntheses of both enantiomers of the indolizidine natural product swainsonine have been achieved in 13 steps from furan. The indolizidine ring system is installed by a one-pot hydrogenolysis of both an azide and an O-Bn group along with an intramolecular reductive amination reaction. The asymmetry of swainsonine was introduced by Noyori reduction of an acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyzed glycosylation, Luche reduction, and a dihydroxylation reaction.