368875-04-1

Basic information

• Product Name: N-benzyloxycarbonyl-D,L-asparagine n-butyl ester
• CAS NO: 368875-04-1
• Molecular Weight: 322.361
• Mol File: 368875-04-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-D,L-asparagine n-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-D,L-asparagine n-butyl ester(368875-04-1)
• EPA Substance Registry System: N-benzyloxycarbonyl-D,L-asparagine n-butyl ester(368875-04-1)

Safety Data

• Hazardous Substances Data: 368875-04-1(Hazardous Substances Data)

Upstream product

• 29880-22-6 N-benzyloxy-carbonyl-DL-asparagine 
• 71-36-3 butan-1-ol 

Downstream Products

• 1219424-59-5 (R)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester 
• 124166-11-6 (S)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester 

Relevant articles and documents

Chemo-enzymatic preparation of chiral 3-aminopyrrolidine derivatives

A new simple method for the enantioselective enzymatic hydrolysis of N-protected D-asparagine esters suitable for the use on the preparative scale is presented. Due to major obstacles observed under conventional reaction conditions - racemization of the retained ester and a strong enzyme inactivation - a comparatively low pH together with an organic co-solvent had to be employed. Under these conditions, nearly all tested proteases demonstrated good activity and excellent enantioselectivity giving access to the corresponding D-esters and L-asparagines in high optical purities (>95% ee) and good chemical yields (>40%). From the unnatural D-asparagine derivative, sequential cyclization, selective deprotection and reduction yielded efficiently benzyl protected (R)-3-aminopyrrolidine, a homo-chiral building block utilized in numerous drug candidates.