2799-12-4

Basic information

• Product Name: N~2~-[(benzyloxy)carbonyl]-alpha-asparagine
• CAS NO: 2799-12-4
• Molecular Formula: C₁₂H₁₄N₂O₅
• Molecular Weight: 266.25
• Mol File: 2799-12-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 560.8°C at 760 mmHg
• Flash Point: 293°C
• Density: 1.355g/cm³
• Vapor Pressure: 2.05E-13mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: N~2~-[(benzyloxy)carbonyl]-alpha-asparagine(CAS DataBase Reference)
• NIST Chemistry Reference: N~2~-[(benzyloxy)carbonyl]-alpha-asparagine(2799-12-4)
• EPA Substance Registry System: N~2~-[(benzyloxy)carbonyl]-alpha-asparagine(2799-12-4)

Safety Data

• Hazardous Substances Data: 2799-12-4(Hazardous Substances Data)

Upstream product

• 4668-43-3 (S)-3-(benzyloxycarbonylamino)-4-ethoxy-4-oxobutanoic acid 
• 64263-86-1 N²-benzyloxycarbonyl-DL-isoasparagine 
• 4515-23-5 N-benzyloxycarbonyl-L-aspartic acid anhydride 
• 1152-61-0 N-Cbz-L-Asp 
• 35739-00-5 benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate 

Downstream Products

• 23632-73-7 N-carbobenzoxy-L-aspartic acid amide 
• 179915-14-1 N²-benzyloxycarbonyl-D-isoasparagine 
• 97533-36-3 N²-benzyloxycarbonyl-L-isoasparagine benzyl ester 
• 51163-34-9 methyl (S)-4-amino-3-(((benzyloxy)carbonyl)amino)-4-oxobutanoate 
• 31883-81-5 (S)-methyl 3-(benzyloxycarbonylamino)-3-cyanopropanoate 

Relevant articles and documents

Enzymatic C-terminal amidation of amino acids and peptides

Herein, we describe two versatile and high yielding enzymatic approaches for the conversion of semi-protected amino acid and peptidyl C-terminal α-carboxylic acids into their corresponding amides. In the first approach, the lipase Candida antarctica lipase-B (Cal-B), and in the second approach, the protease Subtilisin A, are used, respectively. We found that by using the ammonium salt of the α-carboxylic acid instead of separate ammonia sources, the enzymatic amidation reactions proceeded much faster without side reactions and gave near to quantitative yields of products.

Regioselective amidation of aspartic and glutamic acid

The synthesis of N-protected aspartic 1-amide and glutamic 1-amide from aspartic and glutamic acids via regioselective amidation of intermediate 5-oxazolidinone derivatives with aqueous ammonia or amine is described.