72289-51-1

Upstream product

• 507-19-7 t-butyl bromide 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 75-65-0 tert-butyl alcohol 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 501-53-1 benzyl chloroformate 
• 69320-90-7 L-threonine tert-butyl ester hydrochloride 
• 15679-00-2 tert-butyl 2,2,2-trichloroacetimidate 

Downstream Products

• 144923-64-8 N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-threonine tert-butyl ester 
• 144923-61-5 N-benzyloxycarbonyl-O-<3,4,6-tri-O-acetyl-2-(N-2,2,2-trichloroethyloxycarbonyl)-amino-2-deoxy-β-D-glucopyranosyl>threonine tert-butyl ester 
• 521302-84-1 tert-butyl (2S,3R)-2-(benzyloxycarbonyl)amino-3-iodobutanoate 
• 1202236-97-2 C₂₂H₃₇NO₅Si 
• 69320-90-7 L-threonine tert-butyl ester hydrochloride 
• 100325-00-6 N-(Benzyloxycarbonyl)-O-<(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-4,6-di-O-benzoyl-2-desoxy-α-D-galactopyranosyl)>-L-threonin-tert-butylester 

Relevant academic research and scientific papers

Thieme Chemistry Journals Awardees - Where Are They Now? Ribosylation of an Acid-Labile Glycosyl Acceptor as a Potential Key Step for the Synthesis of Nucleoside Antibiotics

Naturally occurring nucleoside antibiotics (e.g., muraymycins and caprazamycins) represent attractive lead structures for the development of urgently needed novel antibacterial agents. One major challenge in the total synthesis of muraymycins, caprazamycins, and their analogues is the efficient construction of the densely functionalized aminoribosylated uridine-derived core unit. In order to avoid tedious protecting-group manipulations, we have aimed to conduct the aminoribosylation step with an acid-labile glycosyl acceptor. Therefore, different glycosylation approaches have been studied, with pentenyl glycosides giving the best results.

Total Synthesis of Seongsanamide B

The first total synthesis of the bicyclic depsipeptide natural product seongsanamide B is described. The successful approach employed solid-phase peptide synthesis of a core heptapeptide, incorporating on-resin esterification, followed by solution-phase macrolactamization and a late stage intramolecular Evans-Chan-Lam coupling to generate the biaryl ether of the isodityrosine unit.

SYNTHESIS AND USE OF HETEROCYCLIC ANTIBACTERIAL AGENTS

This invention relates to compounds of the following Formula (I); or a pharmaceutically acceptable salt, solvate, ester or isomer thereof, which is useful for the treatment of diseases or conditions mediated by LpxC.

Palladium(O) catalysed and copper(I) promoted reactions of the secondary zinc reagent derived from L-threonine

The preparation of C-3 epimeric secondary zinc reagents from diastereoisomeric iodide using DMF as solvent was discussed and analyzed by NMR methods. Palladium catalysed cross couplings and copper promoted allylations produced protected β-methyl substituted amino acids. It was concluded that the threonine derived zinc reagents were of limited values, but further optimization of copper-promoted reactions make this approach to synthesis of β-methyl substituted α-amino acids more useful.

2-Phenyl isopropyl and t-butyl trichloroacetimidates: Useful reagents for ester preparation of N-protected amino acids under neutral conditions

2-Phenylisopropyl and t-butyl trichloroacetamidates 1 and 2 are useful reagents for the esterification of N-protected aminoacids under mild neutral conditions. In the case of hydroxyl-containing amino acids dialkylation occurs but no selectivity could be obtained.

Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for α-amino acid synthesis

(S)-tert-Butyl-N-tert-butoxycarbonylaziridine-2-carboxylate and (S)-tert-butyl-N-tert-butoxycarbonylaziridine-2-carboxamide were synthesised and found to react with copper 'catalysed' Grignard reagents to give protected α-amino acids in moderate to good yields.

Synthetic O-glycopeptides as model substrates for glycosyltransferases

A new approach to O-glycopeptides of the glucosamine type is described. N-Urethane protected, peracetylated glucosamine is converted into its 1-thio (1-bromo) derivative and used for glycosylation of a variety of protected serine or threonine derivatives

Facile synthesis of tert-butyl ester of N-protected amino acids with tert-butyl bromide

A facile synthesis of a wide variety of N-benzyloxycarbonyl-amino acid-tert-butyl ester derivatives under mild conditions is described. N-protected amino acids were esterified with tert-butyl bromide in dimethylacetamide as solvent, in the presence of benzyltriethylammonium chloride (BTEAC)and a large excess of potassium carbonate. Many amino Z-acid-Tert-butyl esters that might be difficult to prepare by other methods have been synthesized in high yields by this procedure. The reaction is simple, unexpansive, easily scaled up, and proceeds without observable racemization.