6602-94-4

Upstream product

• 1170-76-9 Z-Gly-(L)-Phe 
• 5389-16-2 H-Phe-Gly-OEt*HBr 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 459-73-4 GlyOEt*HCl 
• 2899-60-7 Cbz-Gly-ONSuc 
• 41041-68-3 L-phenylalanyl-glycine ethyl ester*HCl 
• 637-81-0 ethyl-2-azidoacetate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 75509-45-4 N-(2-oxido-1,2,3-benzodioxaphosphol-2-yl) glycine ethyl ester 
• 24117-97-3 Z-Gly-L-Phe-OBzl 
• 42567-71-5 L-Phe-Gly-OEt 
• 80681-01-2 [2-Oxo-2-(2-thioxo-thiazolidin-3-yl)-ethyl]-carbamic acid benzyl ester 
• 75509-47-6 tetrabutylammonium salt of N-benzyloxycarbonylglycyl-L-phenylalanine 
• 77374-28-8 C₂₃H₂₈BN₃O₈ 

Relevant academic research and scientific papers

REDOX DEHYDRATION COUPLING CATALYSTS AND METHODS RELATED THERETO

This disclosure relates to synthetic coupling methods using catalytic molecules. In certain embodiments, the catalytic molecules comprise heterocyclic thiolamide, S-acylthiosalicylamide, disulfide, selenium containing heterocycle, diselenide compound, ditelluride compound or tellurium containing heterocycle. Catalytic molecules disclosed herein are useful as catalysts in the transformation of hydroxy group containing compounds to amides, esters, ketones, and other carbon to heteroatom or carbon to carbon transformations.

Processes for forming amide bonds and compositions related thereto

The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

In situ carboxyl activation using a silatropic switch: A new approach to amide and peptide constructions

The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1° and 2° amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.

Condensation between isocyanates and carboxylic acids in the presence of 4-dimethylaminopyridine (DMAP), a mild and efficient synthesis of amides

A mild and convenient method for the preparation of amides from carboxylic acids and isocyanates is described. By using DMAP as a catalyst milder reaction conditions are realised which also allow the conversion of α-chiral isocyanates, as well as α-chiral carboxylic acids without racemisation.

A fast procedure for the preparation of amides/peptides from carboxylic acids and azides via two redox reactions: Application to the synthesis of methionine enkephalin

A one-pot self regulated approach for the synthesis of amides/peptides based on two reduction-oxidation (redox) reactions has been described. The primary and secondary amides/peptides are made by using azidotrimethylsilane and alkyl azides/α-azido acid de

A low-epimerizing peptide coupling reagent based on the rearrangement of a carboxylic-sulfonic mixed anhydride

A series of peptides has been prepared using an o-hydroxybenzenesulfonyl chloride as the condensation reagent. Experimentally, the coupling is a one pot two-steps reaction: formation and aminolysis of a substituted aryl ester. The first step occurs by an

One pot amide/peptide synthesis via two redox reactions

A new and highly efficient one-pot self-regulated approach to amide/peptide synthesis has been developed based on two redox reactions using azide as a latent amine component. For the first time, selenophenol, generated in situ has been found to be effecti

An Improvment of the Anderson Test by the Use of High Performance Liquid Chromatography

The replacement of the N-benzyloxycarbonyl (Z) group in the Anderson peptide (Z-Gly-L/D-Phe-Gly-OEt) by Z-L-Ala and the subsequent separation of the diastereomers of the resulting tetrapeptide by reversed-phase HPLC offer a more convenient version with higher accuracy to the original Anderson test for studying racemization in peptide synthesis.

A New Synthesis of Peptides from Azides and Unactivated Carboxylic Acids

The title reaction, in which an azido compound is treated first with a tertiary phosphine, followed by warming in an inert solvent with a carboxylic acid, has been used to synthesize a number of small peptides and appears from mechanistic studies to proceed via a pentacoordinate phosphorus intermediate.