199786-66-8

Upstream product

• 501-53-1 benzyl chloroformate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100-52-7 benzaldehyde 
• 123639-56-5 methyl (2R)-2-(benzylamino)-3-hydroxypropanoate 
• 40216-75-9 (R)-3-Hydroxy-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester 
• 106-95-6 allyl bromide 
• 199786-65-7 N-benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-D-serinal 

Downstream Products

• 199786-64-6 Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester 
• 199786-63-5 Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-oxo-2-triphenylsilanyloxy-pentyl]-carbamic acid benzyl ester 
• 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.

An efficient stereoselective synthesis of (2S,4S,5R)-(-)-bulgecinine

N-Benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-d-serinal (6) was reacted under Barbier conditions with allyl bromide affording diastereoselectively (82:18) the anti-adduct 5, which was subsequently transformed into (2S,4S,5R)-(-)-bulgecinine (1).

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).