81110-27-2Relevant academic research and scientific papers
Synthesis of Acyl Phosphoramidates Employing a Modified Staudinger Reaction
Currie, Iain,Sleebs, Brad E.
supporting information, p. 464 - 468 (2021/02/03)
A one-step synthesis of acyl phosphoramidates from a variety of functionalized acyl azides has been developed employing trimethylsilyl chloride as an activating agent in a modified Staudinger reaction. The methodology was further adapted to include the in situ generation of the acyl azides from a diverse selection of carboxylic acids and hydrazide starting synthons. The reaction scope was extended to include the synthesis of imidodiphosphates and the natural product Microcin C.
3,3-dichloro-1,2-diphenylcyclopropene (CPICL)-mediated synthesis of n α-protected amino acid azides and α-ureidopeptides
Panguluri, Nageswara Rao,Samarasimhareddy,Madhu,Sureshbabu, Vommina V.
, p. 1001 - 1005 (2014/05/06)
Rapid synthesis of acid azides via in situ generation of acid chlorides using CPICl as chlorinating agent from the corresponding Nα- protected amino acids is described. Also the conversion of acid azides into ureidopeptides through the Curtius rearrangement under ultrasonication is delineated. The mildness of the protocol renders the acid-sensitive substrates to afford the corresponding amino acid azides and ureidopeptides in good yields. Diphenylcyclopropenone has also been recovered from the reaction mixture and reused. Georg Thieme Verlag Stuttgart New York.
New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: Application of peptide coupling agents EDC and HBTU
Sureshbabu, Vommina V.,Lalithamba,Narendra,Hemantha
experimental part, p. 835 - 840 (2010/06/20)
Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved. The Royal Society of Chemistry 2010.
Synthesis of Nα-protected amino acid-derived selenocarbamates employing isocyanates as key intermediates
Sureshbabu, Vommina V.,Naik, Shankar A.
experimental part, p. 2676 - 2685 (2010/11/03)
A simple protocol for the synthesis of Nα-urethane-protected N-alkyl-Se-alkyl selenocarbamate derivatives of amino acids has been described. The reaction of Nα-urethane-protected amino alkyl isocyanates with selenating agent LiAlHSeH and subsequent coupli
Efficient synthesis of O-succinimidyl-(tert-butoxycarbonylamino)methyl carbamates derived from α-amino acids accelerated by ultrasound: Application to the synthesis of ureidodipeptides
Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Kantharaju
, p. 2168 - 2184 (2008/09/21)
The synthesis of O-succinimidyl-(tert-butoxycarbonylamino)methyl carbamates employing isocyanates made through the Curtius rearrangement of Boc-amino acid azides in the presence of N-hydroxysuccinimide under the influence of ultrasound is described. Copyright Taylor & Francis Group, LLC.
Pentafluorophenyl-(tert-butoxycarbonylamino) methylcarbamates: Synthesis, isolation and application to the synthesis of ureidopeptides
Sureshbabu, Vommina Venkata,Narendra,Kantharaju
, p. 920 - 926 (2008/12/23)
The one-pot synthesis of pentafluorophenyl-(tert-butoxycarbonylamino)methyl carbamates starting from N-Boc amino acids is described. Ultrasound mediated concomitant rearrangement and coupling reactions have resulted in the production of good yields of the active methyl carbamates. The carbamates have been employed as monomeric building blocks for the synthesis of dipeptidyl urea esters/acids. All the compounds obtained have been fully characterized by IR, 1H NMR, 13C NMR and mass spectroscopy.
Succinimidyl carbamate derivatives from N-protected α-amino acids and dipeptides-synthesis of ureidopeptides and oligourea/peptide hybrids
Fischer, Lucile,Semetey, Vincent,Lozano, Jose-Manuel,Schaffner, Arnaud-Pierre,Briand, Jean-Paul,Didierjean, Claude,Guichard, Gilles
, p. 2511 - 2525 (2008/03/13)
The preparation of succinimidyl (1-{[(alkyloxy)carbonyl]-amino}-1-X-methyl) carbamates (4) and succinimidyl [1-(acyl-amino)-1-X-methyl] carbamates (5) from a variety of N-Boc-, -Z- or -Fmoc-protected α-amino acids and dipeptides as well as the carbamate s
Retro-Inverso Isomerization of Peptides: Side Reactions in the Synthesis of N,N'-Diacyl-1,1-diamino-2-phenylethane Derivatives
Chorev, Michael,MacDonald, Scott A.,Goodman, Murray
, p. 821 - 827 (2007/10/02)
In general, the synthesis of retro-inverso peptides requires the formation of diacylated gem-diaminoalkyl structures.One way to prepare these gem-diaminoalkyl residues involves the Curtius rearrangement of the N-acylated amino acid hydrazides to the corre
A Novel Synthesis of Peptide Based on the Photochemistry of 5-Azido-1,3,4-oxadiazoles
Confalone, Pat N.,Woodward, Robert B.
, p. 902 - 906 (2007/10/02)
A novel approach to the synthesis of peptides is described.Various N-protected amino acid hydrazides 17 were converted to the salts 18 by condensation with carbon disulfide in methanolic potassium hydroxide.Thermal cyclization of 18 to the heterocycles 19 was followed by reaction with methyl iodide to yield the sulfides 20.After oxidation of 20 to the corresponding sulfones 21, the title compounds 22 were prepared by treating 21 with sodium azide.Deprotection then yielded the free bases 23.Utilization of 22 and 23 in peptide synthesis, relying on a photochemical degradation of the title heterocycle present in these compounds, is described.The scope and limitations of this new methodology are also discussed.
