174874-82-9

Upstream product

• 2393-23-9 4-methoxy-benzylamine 
• 59025-03-5 (S)-acetoxysuccinic anhydride 
• 97-67-6 (S)-Malic acid 
• 75-36-5 acetyl chloride 

Downstream Products

• 174874-98-7 (S)-2-[(2R,3S)-3-Acetoxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-2-yl]-7-(tert-butyl-diphenyl-silanyloxy)-3-oxo-octanoic acid ethyl ester 
• 174874-87-4 (2R,3S)-2-<3-acetoxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-2-yl>-3-oxo-butyric acid methyl ester 
• 174874-84-1 acetic acid (2S,3S)-2-acetoxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-3-yl ester 
• 254730-11-5 C₂₉H₃₃NO₈S₂ 
• 254730-08-0 (S)-4-Benzyloxy-5-(3-benzyloxy-propyl)-5-hydroxy-1-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 254730-09-1 (+)-(4S,5R)-4-benzyloxy-5-(3'-benzyloxypropyl)-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 254730-07-9 (S)-4-benzyloxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione 

Relevant academic research and scientific papers

A study on the racemization step in the synthesis of pyrrolidinols via cyclic α-hydroxyimides

Analytical HPLC methods for the determination of the enantiomeric excess of N-protected malimides 1 as well as the corresponding pyrrolidinol 5 and tartarimides 2 and 3 have been established. On this basis, a study to reveal the racemization step in the synthesis of pyrrolidinols from α-hydroxyacids, via chiral cyclic α-hydroxyimides, has been undertaken. It was confirmed that the known, one-step method for the synthesis of the N-protected chiral cyclic imides from α-hydroxydiacids proceeded with little racemization, and partial racemization has been proven to occur during the reduction of the resultant imide 1a with LAH to yield the corresponding pyrrolidinol 5. Conditions have been defined in order to avoid racemization in the LAH reduction step.

Studies towards the synthesis of (+)-ptilomycalin A; stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams

Highly stereoselective N-acyliminium ion coupling reactions of β-ketoester derived silyl enol ethers with enantiopure lactams derived from (S)-malic acid are reported. This reaction type is applied in the synthesis of the enantiopure C-2 substituted lactam 27, a plausible intermediate in a projected synthesis of ptilomycalin A.