A Facile Synthesis of N-fmoc Protected Amino/peptidyl Weinreb Amides Employing Acid Chlorides as Key Intermediates

An efficient, cost effective method for the preparation of N-Fmoc α-amino/ peptidyl Weinreb amides from the corresponding acid chlorides has been described. The synthesis of acid chlorides was accelerated by ultrasonication and were coupled with N,O -dimethylhydroxylamine hydrochloride to obtain the title compounds. All the prepated compound were isolated as stable solids after workup and have been fully characterized by IR, 1H NMR,13C NMR and mass spectroscopy

ChemInform Abstract: Efficient Synthesis of N‐Fmoc‐Aminoalkoxy Pentafluorophenyl Carbonates: Application for the Synthesis of Oligopeptidyl Carbamates

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option

A simple approach for the synthesis of new classes of dithiocarbamate-linked peptidomimetics

An efficient protocol for the synthesis of a new series of dithiocarbamate-linked peptidomimetics is described. The in situ generated dithiocarbamic acid intermediate formed by the reaction of an amino acid ester and carbon disulfide in the presence of triethylamine was treated with N-protected amino alkyl iodide to afford title compounds 3a–g in good to moderate yields. The synthesis of N-Fmoc-protected tripeptidomimetics 4a–e containing two dithiocarbamate linkages is also described. The protocol was further extended to synthesize N,N′-orthogonally protected dithiocarbamate-linked dipeptidomimetics 7a–c as well. The mild reaction conditions and non-toxic reagents are the advantages of the present method

A Facile Synthesis of C-terminal Neoglycopeptides: Incorporation of Urea Moiety between Sugars and Peptides Employing Curtius Rearrangement

Incorporation of urea moiety in the synthesis of C-terminal neoglycopeptides has been demonstrated through the reaction between suitably protected glycosylamine and Fmoc-peptidyl isocyanates or carbamates. Curtius rearrangement has been made use off for the conversion of peptidyl acid azides in to corresponding isocyanates. The resulting C-terminal neoglycopeptidylureas have been isolated as stable solids which are fully characterized by 1H NMR and mass spectroscopy

A simple protocol for the synthesis of triazole-linked cyclic glycopeptidomimetics: A sequential Ugi-MCR and azide-alkyne cycloaddition approach

Sequential combination of Ugi-MCR and click chemistry has been employed for the synthesis of triazole linked cyclic glycopeptidomimetics. The protocol employs Poc-amino alkyl isonitriles, sugar-1-amines, azido acids, and simple aldehydes as precursors. The dual nature of the propargyloxycarbonyl (Poc) group was explored for amine protection as well as cycloaddition with an azide. All the cyclic glycopeptidomimetics are isolated and characterized. © 2012 Elsevier Ltd. All rights reserved

ChemInform Abstract: Synthesis of Urea Tethered Glycosylated Amino Acids and Glycopeptides Mediated by DPPA Employing Nα‐Fmoc‐Asp/Glu‐5‐oxazolidinones

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option

ChemInform Abstract: 1‐Propanephosphonic Acid Cyclic Anhydride (T3P) as an Efficient Promoter for the Lossen Rearrangement: Application to the Synthesis of Urea and Carbamate Derivatives.

A convenient procedure is presented for the conversion of aromatic acids and amino acids into hydroxamates using T3P as activator

Simple Preparation of N-Protected Chiral β-Amino Alkyl Thiols from Corresponding Iodides Employing Sodium Trithiocarbonate

A simple protocol for the preparation of N-protected amino alkyl thiols is reported that employs a reaction of sodium trithiocarbonate (Na2CS3) with N-protected amino alkyl iodides. Na2CS3 is easy to prepare and the protocol circumvents the use of strong bases and multiple steps. All the thiol compounds made were obtained as enantiopure samples and were characterized employing NMR and mass spectrometry

Isoselenocyanates derived from Boc/Z-amino acids: Synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The 1H NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenoureido derivatives is free from racemization. © 2010 Elsevier Ltd. All rights reserved