131990-99-3

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 131990-98-2 2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-glucose propane-1,3-diyldithioacetal 
• 3416-24-8 2-amino-2-deoxyglucose 
• 72022-71-0 2-amino-2-deoxy-D-glucose propane-1,3-diyldithioacetal hydrochloride 

Downstream Products

• 131991-01-0 1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3β-methoxy-4β-styryl-2-azetidinone 
• 132075-32-2 1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3α-methoxy-4α-styryl-2-azetidinone 
• 132075-33-3 [(3S,4R)-2-Oxo-4-((E)-styryl)-azetidin-3-yl]-carbamic acid tert-butyl ester 
• 131991-02-1 (3S,4R)-3-Amino-1-[(R)-[1,3]dithian-2-yl-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-4-((E)-styryl)-azetidin-2-one 
• 131991-03-2 [(3S,4R)-1-[(R)-[1,3]Dithian-2-yl-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-2-oxo-4-((E)-styryl)-azetidin-3-yl]-carbamic acid tert-butyl ester 
• 132075-34-4 3α-methoxy-4α-styryl-2-azetidinone 
• 131991-05-4 3β-methoxy-4β-styryl-2-azetidinone 

Relevant academic research and scientific papers

ASYMMETRIC SYNTHESIS OF 1,3,4-TRISUBSTITUTED AND 3,4-DISUBSTITUTED 2-AZETIDINONES: STRATEGY BASED ON USE OF D-GLUCOSAMINE AS A CHIRAL AUXILIARY IN THE STAUDINGER REACTION.

An efficient asymmetric approach to the synthesis of trisubstituted azetidin-2-ones is presented.The strategy relies on the use of ketene-imine cycloaddition between ketenes generated from phtalimidoacetic and methoxyacetic acids and a chiral Schiff base (3) derived from 3,4,;5,6-di-O-isopropylidene-D-glucosamine propane dithioacetal (2) and cinnamaldehyde; the removal of the chiral auxiliary group by β-elimination is a noteworthy facet af this communication.