756846-17-0

Upstream product

• 57653-38-0 N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 2232-08-8 N-tosylimidazole 
• 98-59-9 p-toluenesulfonyl chloride 
• 102013-10-5 (2S,4R)-1-[(benzyloxy)carbonyl]-4-(p-toluenesulfonyloxy)pyrrolidine-2-formic acid 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

A inhibiting DPP-IV compounds and intermediates

Provided are compounds as presented in formulas IA or IB or pharmaceutically acceptable salts thereof, the preparation method therefor, and uses thereof. Also provided are the intermediates of the compounds and the preparation method therefor. The compounds of the present invention can effectively inhibit DPP-IV activity. Compared to the commercial available medicine, Januvia, compound 1 exhibits strong inhibition against DPP4, but has lower activity inhibition against other DPP family members (DPP2, DPP8, and DPP9). Hence the compound of the present invention can not only effectively inhibit DPP4 from exhibiting medicinal activity, but also lower the activity inhibition against other members of the DPP family, reduce toxic side effect, and have better medicinal safety.

Novel asymmetric approach to proline-derived spiro-β-lactams

We describe a novel asymmetric approach using Staudinger chemistry to proline-derived spiro-β-lactams. A chiral group at C-4 of the acid chloride of proline directs the stereoselectivity of Staudinger chemistry and later is sacrificed to obtain optically active 5.4-spiro-β-lactams. The scope, limitations, and mechanistic rationale for the observed results of Staudinger Chemistry of the acid chloride of 4-alkyl(aryl)sulfonyloxy-L-proline with imines are also discussed.