199786-63-5

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 501-53-1 benzyl chloroformate 
• 123639-56-5 methyl (2R)-2-(benzylamino)-3-hydroxypropanoate 
• 76-86-8 Triphenylsilyl chloride 
• 199786-66-8 Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester 
• 199786-64-6 Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester 
• 199786-65-7 N-benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-D-serinal 
• 199786-67-9 Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-2-triphenylsilanyloxy-pentyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of 1,3-dideoxynojirimycin via an α-amino aldehyde as a key intermediate

1,3-Dideoxynojirimycin was synthesized starting from a suitably protected α-amino aldehyde. The crucial step involves addition of allyl bromide to N-benzyl-N-carbobenzoxy-O-tert-butyldimethylsilyl-D-serinal in the presence of tin(II) chloride and sodium iodide.

Total synthesis of 1,3-dideoxynojirimycin

Addition of allyl bromide (5) to N-benzyl-N-carbobenzoxy-O-tert- butyldimethyl-D-serinal (4) afforded with high diastereoselectivity anti- adduct 6 which subsequently transformed into (2R,4S,5R)-1,3- dideoxynojirimycin (1).