132075-32-2

Upstream product

• 38870-89-2 Methoxyacetyl chloride 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 3416-24-8 2-amino-2-deoxyglucose 
• 72022-71-0 2-amino-2-deoxy-D-glucose propane-1,3-diyldithioacetal hydrochloride 
• 135565-72-9 2-amino-2-deoxy-D-glucose propane-1,3-diyldithioacetal 
• 131990-99-3 [(R)-[1,3]Dithian-2-yl-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[(E)-3-phenyl-prop-2-en-(Z)-ylidene]-amine 
• 131990-98-2 2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-glucose propane-1,3-diyldithioacetal 

Downstream Products

• 131991-04-3 1-deoxy-1-(1,3-dithiane-2-ylidene)2,3;4,5-di-O-isopropylidene-D-arabinitol 
• 132075-34-4 3α-methoxy-4α-styryl-2-azetidinone 

Relevant academic research and scientific papers

D-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-lactam chemistry

The synthesis of some monocyclic β-lactams (monobactams) by the Staudinger reaction using d-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C3, C4, and C(1') (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity. Copyright (C) 1999 Elsevier Science Ltd.

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.