199786-65-7

Upstream product

• 40216-75-9 (R)-3-Hydroxy-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester 
• 123639-56-5 methyl (2R)-2-(benzylamino)-3-hydroxypropanoate 
• 100-52-7 benzaldehyde 
• 158012-74-9 N-benzyl-N-benzyloxycarbonyl-L-serine methyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 501-53-1 benzyl chloroformate 
• 209266-11-5 (S)-2-(Benzyl-benzyloxycarbonyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 
• 123639-56-5 (S)-N-benzylserine methyl ester 
• 209266-18-2 Benzyl-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-carbamic acid benzyl ester 

Downstream Products

• 199786-66-8 Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-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 
• 199786-64-6 Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

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).

Effective and mild method for preparation of optically active α-amino aldehydes via TEMPO oxidation

The TEMPO oxidation method is successfully applied to preparation of variously protected, optically active α-amino aldehydes without racemization and in very good yield.

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).