- Synthesis of Nα-Z protected amino alkyl triazole acids and their application to neo-glycopeptides synthesis
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The synthesis of triazole linked glycopeptides employing 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) mediated coupling of Z-protected triazole acids with glycosyl amines and amino acid esters is described. The coupling proceeded smoothly at room temperat
- Madhu, Chilakapati,Panguluri, Nageswara Rao,Sureshbabu, Vommina V.
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p. 858 - 864
(2014/08/05)
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- Stereoselective synthesis of chiral pyrrolidine derivatives of (+)-α-pinene containing a β-amino acid moiety
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We report the synthesis of several enantiopure pyrrolidine derivatives containing a β-amino acid moiety. These novel chiral compounds were prepared through stereospecific chlorosulfonyl isocyanate (CSI) addition to the readily available, natural terpene (+)-α-pinene. Coupling of N-Boc-protected β-amino acid derivatives with various bulky amines and amino acids using the mixed anhydride activation method, followed by N-deprotection, afforded the corresponding chiral amino amides in good yields. Despite the severe steric hindrance anticipated in α-pinene-based heterocycles, efficient coupling of the amino amides and an amino ester with the acyl chloride of N-Cbz-protected (S)-proline provided the corresponding pyrrolidinic pinene derivatives in good yields. Moreover, a convenient synthesis of N-Cbz- and N-Boc-monoprotected (S)-prolinamine is reported. Georg Thieme Verlag Stuttgart New York.
- Vega-Penaloza, Alberto,Sanchez-Antonio, Omar,Escudero-Casao, Margarita,Tasnadi, Gabor,Fueloep, Ferenc,Juaristi, Eusebio
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p. 2458 - 2468
(2013/09/23)
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- Synthesis of chiral NADH analog based on proline template including thiourea and nicotinic acid moieties
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Chiral reductase-mimicking organic molecule built on proline template incorporating a covalently bound NADH mimic via thiourea, and related reducing agent Hantzsch dihydropyridine, was designed. A synthetic path was developed involving interlinking of chiral proline derivatives with thiourea and subsequent coupling reaction with nicotinoyl chloride. The structure of target compound was studied by x-ray, indicating a double H bond with thiourea hydrogens and oxygen O1 of benzylcarbamate fragment. The reduction of benzil and imines was performed. Taylor & Francis Group, LLC.
- Bagdziunas, Gintautas,Haukka, Matti,Butkus, Eugenijus
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experimental part
p. 2517 - 2523
(2011/08/07)
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- Asymmetric organocatalysis of the addition of acetone to 2-nitrostyrene using N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine (PODPEN)
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The highly enantioselective addition of acetone to 2-nitrostyrene, using N-diphenylphosphinyl-trans-1,2-diphenylethane-1,2-diamine (PODPEN) as a catalyst, is described.
- Morris, David J.,Partridge, A. Simon,Manville, Charles V.,Racys, Daugidas T.,Woodward, Gary,Docherty, Gordon,Wills, Martin
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supporting information; experimental part
p. 209 - 212
(2010/03/24)
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- Efficient synthesis of fused 1,2,3-triazolo-δ-lactams using Huisgen [3 + 2] dipolar cycloaddition "click-chemistry" in water
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A general approach for the quick synthesis of various 1,2,3-triazolo- δ-lactams has been described, which involves the Huisgen [3 + 2] dipolar cycloaddition of azides derived from different amino acids with dimethyl acetylenedicarboxylate in water followe
- Kumar, Indresh,Rode, Chandrashekhar V.
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p. 592 - 593
(2008/02/07)
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- Synthesis of (D)- And (L)-forms of differentially protected 2-piperidinemethanamine
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(D)- and (L)-isomers of pipecolic acid were converted into (D)- and (L)-2-piperidinemethanamine using an efficient sequence. The amino groups were selectively protected for further functionalization.
- Perumattam, John,Shearer, Barry G.,Confer, William L.,Mathew, Rose M.
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p. 7183 - 7186
(2007/10/02)
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