1326775-96-5

Basic information

• Product Name: N-tert-butoxycarbonyl-L-phenylalanyl-N(γ)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-L-aspargine methyl ester
• Synonyms: N-tert-butoxycarbonyl-L-phenylalanyl-N(γ)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-L-aspargine methyl ester
• CAS NO: 1326775-96-5
• Molecular Weight: 723.731
• Mol File: 1326775-96-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-tert-butoxycarbonyl-L-phenylalanyl-N(γ)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-L-aspargine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-butoxycarbonyl-L-phenylalanyl-N(γ)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-L-aspargine methyl ester(1326775-96-5)
• EPA Substance Registry System: N-tert-butoxycarbonyl-L-phenylalanyl-N(γ)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-L-aspargine methyl ester(1326775-96-5)

Safety Data

• Hazardous Substances Data: 1326775-96-5(Hazardous Substances Data)

Upstream product

• 1326775-92-1 Cbz-Asp(SPy)-OMe 
• 1326775-93-2 N(α)-benzyloxycarbonyl-N(γ)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-L-aspargine methyl ester 
• 1326775-95-4 C₂H₄O₂*C₁₉H₂₈N₂O₁₂ 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 1326776-06-0 N(γ)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-L-aspargine O-methyl ester hydrochloride 
• 4668-42-2 (S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester 
• 525589-11-1 2-methyl-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline 
• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 

Relevant articles and documents

Synthesis of α-N-linked glycopeptides

A practical synthesis of Nα-fluorenylmethoxycarbonyl- Nγ-(2,3,4,6-tetra-O-acetyl-α-D-glycopyranosyl)-L- asparagine in the gluco and galacto series has been achieved by using the methodology developed by DeShong and co-workers. The resulting α-N-linked glycosyl amino acids were used in a linear approach to the synthesis of glycopeptides featuring the unnatural α-N-glycosyl linkage. Activation conditions for both C- and N-terminus elongation in solution have been defined. The main side-reaction encountered was the formation of cyclization by-products (aspartimide) from the activated amino acid during C-terminus elongation. Appropriate condensing agents were identified, which allowed a high yield of dipeptide formation and no epimierization of the glycosyl amino acids. Conditions for sugar deacetylation have also been optimized. Solid-phase synthesis (Fmoc protocol) conditions were explored and PyBROP was found to be the reagent of choice for the activaton of glycosyl amino acids. The synthesis of more complex α-N-linked glycopeptides has thus become feasible, which will allow the properties of these neo-glycoconjugates to be studied. Copyright