1380332-87-5

Basic information

• Product Name: Cbz-(L)-leucyl-(D)-prolyl benzotriazole
• Synonyms: Cbz-(L)-leucyl-(D)-prolyl benzotriazole
• CAS NO: 1380332-87-5
• Molecular Weight: 463.536
• Mol File: 1380332-87-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Cbz-(L)-leucyl-(D)-prolyl benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-(L)-leucyl-(D)-prolyl benzotriazole(1380332-87-5)
• EPA Substance Registry System: Cbz-(L)-leucyl-(D)-prolyl benzotriazole(1380332-87-5)

Safety Data

• Hazardous Substances Data: 1380332-87-5(Hazardous Substances Data)

Upstream product

• 2018-66-8 Z-Leu-OH 
• 95-14-7 1,2,3-Benzotriazole 

Downstream Products

• 1380332-79-5 cyclo(Z-L-Leu-D-Pro) 
• 2873-36-1 (3S,8aR)-3-isobutyl-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant articles and documents

A new benzotriazole-mediated stereoflexible gateway to hetero-2,5- diketopiperazines

Open chain Cbz-L-aa1-L-Pro-Bt (Bt=benzotriazole) sequences were converted into either the corresponding trans- or cis-fused 2,5- diketopiperazines (DKPs) depending on the reaction conditions. Thermodynamic tandem cyclization/epimerization afforded selectively the corresponding trans-DKPs (69-75%). Complementarily, tandem deprotection/cyclization led to the cis-DKPs (65-72%). A representative set of proline-containing cis- and trans-DKPs has been prepared. A mechanistic investigation, based on chiral HPLC, kinetics, and computational studies enabled a rationalization of the results. Stereoflexible route to DKPs: A convenient, versatile, and flexible benzotriazole-mediated methodology for the synthesis of proline-containing hetero-2,5-diketopiperazines (DKPs) is reported. Depending on the reaction conditions, either cis- or trans-configured DKPs were obtained starting from the same inexpensive l,l-dipeptidoyl benzotriazole key intermediate (see scheme). Kinetics, chiral HPLC, and computational studies forged a background for mechanistic rationalization. Copyright