848047-83-6

Upstream product

• 2304-96-3 N-benzyloxycarbonyl-L-asparagine 
• 106-95-6 allyl bromide 

Downstream Products

• 1182846-85-0 N^α-(benzyloxycarbonyl)-N^γ-(6-O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-3-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranosyl)-L-asparagine allyl ester 
• 1200438-00-1 (2S,6S)-4-oxo-2-phenyltetrahydropyrimidine-1,6(2H)-dicarboxylic acid 6-allyl ester 1-benzyl ester 
• 1200437-96-2 (2R,6S)-4-oxo-2-phenyltetrahydropyrimidine-1,6(2H)-dicarboxylic acid 6-allyl ester 1-benzyl ester 
• 99701-64-1 N-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)-methyl)-tetrahydro-2H-pyran-2-yl)-2,2,2-trichloroacetamide 
• 66963-55-1 1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranose 
• 1182846-84-9 C₅₃H₅₂Cl₃N₃O₁₃ 

Relevant academic research and scientific papers

Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups

The efficient and elegant synthesis of N-glycosides by N-glycosylation of asparagine-containing peptides is described. Glycosylation of primary amides with glycosyl N-phenyltrifluoroimidates in the presence of a catalytic amount of TMSOTf in nitromethane

Simplified beta-glycosylation of peptides

A simple and effective activating system for S-phenyl thioglycosides, namely N-iodosuccinimide and catalytic copper(I) triflate, promotes beta-O-glycosylation at the serine and threonine hydroxyls of “mono-,” di-, and tripeptides. The same activator combination promotes carboxamide beta-N-glycosylation of asparagine-containing mono-, di, and tri-peptides, as well as a nucleoside carboxamide and a sulfonamide. An important feature of the copper(I) triflate method is that undesired amide O-glycosylation is largely circumvented. For both sets of biologically important acceptor sites (HO– and –CONH2), a beta-GlcNAc-equivalent donor is demonstrated to provide the linkages efficiently. Streamlined deprotection sequences have been developed based on global hydrogenolysis that lead smoothly to the parent glycopeptides. The core glycopeptide region for biological protein N-glycosylation, represented by N4-(β-N-acetyl-D-2-glucosaminyl)-Asp-Gly-Thr-OH, has been prepared in solution, purified, and characterized as the fully deprotected (mono)glycosylated tripeptide.

2-Phenyl-tetrahydropyrimidine-4(1H)-ones - Cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised β2-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free β2-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R)-β2-homoaspartate.