383416-20-4

Upstream product

• 2745-22-4 2-(1-hydroxy-2-aminoethyl)-furan 
• 52239-33-5 1-(furan-2-yl)-2-nitroethanol 
• 98-01-1 furfural 
• 383416-19-1 (+/-1)-(2-furan-2-yl-2-hydroxyethyl)carbamic acid benzyl ester 

Downstream Products

• 226254-73-5 (1R)-(2-furan-2-yl-2-hydroxy-ethyl)-carbamic acid benzyl ester 
• 438044-17-8 (2R,5R,6R)-4'-nitrobenzoic acid 2-(benzyloxycarbonylamino-methyl)-6-(2,2-dimethyl-propionyloxy)-5,6-dihydro-2H-pyran-3-yl ester 
• 383416-22-6 (2R,6R)-2,2-dimethyl-propionic acid 6-(benzyloxycarbonylamino-methyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester 
• 383416-24-8 (2R,5S,6R)-2,2-dimethyl-propionic acid 6-(benzyloxycarbonylamino-methyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl ester 
• 438044-09-8 (2R,5R,6R)-2,2-dimethyl-propionic acid 6-(benzyloxycarbonylamino-methyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl ester 
• 383416-21-5 (2R)-6-hydroxy-2-N-benzyloxycarbonylaminomethyl-2H-pyran-3(6H)-one 

Relevant academic research and scientific papers

De novo asymmetric approaches to 2-amino-n-(Benzyloxycarbonyl)-1-(2'fury)ethanol and 2-amino-n-(tert-butoxycarbonyl)-1-(2'furyl)ethanol

Several methods were investigated for the de novo asymmetric synthesis of 2-amino-N-(benzyloxycarbonyl)-1-(2'-furyl)ethanol and 2-amino-N-(tert-butoxycarbonyl)-1-(2'-furyl)ethanol. A five step procedure was developed for the practical preparation of optically pure 2-amino-N-benzyloxycarbonyl)-1-(2'-furyl)ethanol and a shorter 2-step procedure was developed for 2-amino-N-(tert-butoxycarbonyl)-1-(2'-furyl)ethanol. Both routes used a Noyori reduction to install the asymmetry.

Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose

equation presented The enantioselective synthesis of three 6-amino-6-deoxy sugars has been achieved in six to eight steps from furfural. A sequence of diastereoselective oxidation and reduction reactions produced Cbz-protected 6-aminomannose from furfuryl alcohol 3. The incorporation of a Mitsunobu reaction into the reaction sequence allows for the selective synthesis of both N-Cbz-protected 6-aminotalose and 6-aminogulose. The overall procedure allows for the synthesis of either enantiomer of these three aminosugars.