613244-60-3

Upstream product

• 67124-60-1 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide 
• 613244-82-9 Boc-Hcy-Ala-OBn 
• 676602-45-2 (S)-2-{(S)-4-[(S)-3-((S)-1-Benzyloxycarbonyl-ethylcarbamoyl)-3-tert-butoxycarbonylamino-propyldisulfanyl]-2-tert-butoxycarbonylamino-butyrylamino}-propionic acid benzyl ester 
• 130981-51-0 (2S,2'S)-4,4'-disulfanediylbis(2-(tert-butoxycarbonyl)amino)butanoic acid 
• 5557-81-3 L-alanine benzyl ester hydrochloride 

Downstream Products

• 676602-53-2 (S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester 
• 613244-61-4 N-tert-butoxycarbonyl-S-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-homocysteinyl-L-alanine benzyl ester 

Relevant academic research and scientific papers

Selective conversion of N-trichloroethoxycarbonyl (Troc) groups into N-acetyl groups in the presence of N-tert-butoxycarbonyl (Boc) protecting groups

Deprotection of N-trichloroethoxycarbonyl (Troc) groups with zinc in acetic anhydride cleaves also N-tert-butoxycarbonyl (Boc) groups, thus liberating the amino groups, which are immediately N-acetylated. When this reaction is performed in the presence of triethylamine only Troc groups are selectively cleaved as demonstrated for several examples.

Synthesis of an S-linked glycopeptide analog derived from human Tamm-Horsfall glycoprotein

Direct base catalyzed S-glycosylation of a cysteine and a homocysteine containing peptide with O-acetyl protected bromides in DMF-water solution furnished two glycopeptide fragments. The two glycopeptide fragments were linked to the target glycopeptide with two S-glycosyl residues mimicking a part of Tamm-Horsfall glycoprotein.