149356-12-7

Upstream product

• 100-39-0 benzyl bromide 
• 128459-42-7 (3R,4S)-N-(tert-Butoxycarbonyl)-4,5-N,O-isopropyliden-4-amino-3,5-dihydroxy-1-(2-thiazolyl)-1-pentanone 
• 128525-58-6 (S)-4-((1R,3S)-1,3-Dihydroxy-3-thiazol-2-yl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 149406-11-1 (1S,3R,4S)-1,3-dibenzyloxy-5-hydroxy-4,5-N,O-isopropylidene-4-(tert-butoxycarbonylamino)-1-(2-thiazolyl)pentane 

Relevant academic research and scientific papers

Totally chemical synthesis of azasugars via thiazole intermediates. Stereodivergent routes to (-)-nojirimycin, (-)-mannojirimycin and their 3-deoxy derivatives from serine

The synthesis of the (-)-antipodes of the natural products nojirimycin (+)-1 and mannojirimycin (+)-2 has been carried out by stereocontrolled reduction of the thiazole ketone 7 as a common key intermediate. This ketone was in turn obtained from the L-serine derived aldehyde 3 by two convergent routes involving carbonylolefination and dihydroxylation processes. Moreover, 3-deoxy derivatives of (-)-1 and (-)-2 have been prepared from 3 and the lithium enolate of 2-acetylthiazole followed by stereocontrolled reduction of the resultant aldol.