85995-51-3

Upstream product

• 5618-95-1 N-benzyloxycarbonyl-DL-threonine 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 
• 5618-95-1 N-CBZ-D,L-allo-threonine 
• 72-19-5 rac-allo-threonine 
• 501-53-1 benzyl chloroformate 
• 212632-22-9 (2S,3R)-2-Benzyloxycarbonylamino-3-tert-butoxy-butyric acid benzyl ester 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 100-39-0 benzyl bromide 
• 5618-95-1 2-benzyloxycarbonylamino-3-hydroxy-butyric acid 

Downstream Products

• 101890-79-3 2-benzyloxycarbonylamino-acetoacetic acid benzyl ester 
• 146900-31-4 (2S,3R)-2-Benzyloxycarbonylamino-3-(benzyloxy-diisopropylamino-phosphanyloxy)-butyric acid benzyl ester 
• 77871-00-2 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-L-threonine 
• 77871-00-2 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-L-threonine 
• 83982-55-2 N-(Benzyloxycarbonyl)-3-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-L-threoninbenzylester 
• 121542-13-0 (2S,3R)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-benzyloxycarbonylamino-butyric acid benzyl ester 
• 121542-13-0 (S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-benzyloxycarbonylamino-butyric acid benzyl ester 
• 1027379-74-3 Hexanoic acid (R)-2-[((1R,2S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phenoxy-phosphanyloxy]-1-hexanoyloxymethyl-ethyl ester 
• 84520-34-3 benzyl N-benzyloxycarbonyl-(Z)-α-aminobut-2-enoate 
• 96043-06-0 3-O-<2-Acetamido-4,6-di-O-benzoyl-2-desoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-N-benzyloxycarbonyl-L-threoninbenzylester 

Relevant academic research and scientific papers

13C NMR Spectroscopy, a Useful Tool To Determine the Enantiomeric Purity of Synthetic Threonine-Containing Glycopeptides. Spectra of Diastereoisomeric α- and β-D-Galactopyranosyl-L- and -D-threonine and -L- and -D-allothreonine

Further studies of O-glycosyl amino acids by natural-abundance 13C NMR spectroscopy are presented.Carbon-13 NMR spectra of diastereoisomeric α- and β-D-galactopyranosyl-L-threonine, -D-threonine, -L-allothreonine, and -D-allothreonine showed distinct anom

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.

Site-selective solid phase synthesis of carbonylated peptides

Abstract The aim of our research was to design an efficient method for the solid phase synthesis of carbonylated peptides. For this purpose, we designed and synthesized a fully protected derivative Fmoc-amino(2,5,5-trimetyhyl-1,3-dioxolan-2-yl)acetic acid

Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers

(Chemical Equation Presented) Aqueous phosphoric acid (85 wt %) is an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers. The mildness of the reaction is further demonstrated in the synthesis of clarithromycin derivative 4, in which a tert-butyl ester is removed in the presence of cyclic carbamate, lactone, ketal, acetate ester, and epimerizable methyl ketone functionalities. The reaction preserves the stereochemical integrity of the substrates. The reactions are high yielding, and the workup is convenient.