325699-99-8

Upstream product

• 325699-97-6 (2R)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 91174-01-5 sodium [(benzyloxy)carbonyl]chloroamide 
• 325699-88-5 (2R)-2-(tert-butyldimethylsilyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 226254-77-9 (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester 
• 621-84-1 O-benzyl carbamate 
• 1578-26-3 1-(2'-furyl)-2-trimethylsilanylethan-1-ol 
• 98-01-1 furfural 
• 1487-18-9 (furan-2-yl)ethylene 

Downstream Products

• 325700-14-9 (2R,3R,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3,4,5-trihydroxy-piperidine-1-carboxylic acid benzyl ester 
• 325700-10-5 (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 325700-28-5 (2R,3S)-6-ethoxy-3-hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 14199-63-4 1-deoxymannojirimycin 
• 325700-26-3 (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 325700-04-7 (2R,3S,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3,4,5-trihydroxypiperidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of D- and L-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran

(Equation Presented) The Sharpless catalytic asymmetric aminohydroxylation has been applied to 2-vinylfuran, producing β-hydroxyfurfurylamine 5a with enantioexcess of >86% and 21% yield from furfural. The Cbz and TBS protected amino alcohol 5a was converted into both the D- and L-isomers of deoxymannojirimycin (DMJ) and deoxygulonojirimycin in five to seven steps and 48% and 66% overall yields. The key steps include the use of an aza-Achmatowicz reaction, a diastereoselective Luche reduction, diastereoselective dihydroxylation, and a tandem Cbz deprotection/reductive amination.