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Synthesis of esters derived from 2,3,4,6-tetra-O-acetyl-1-[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]-beta-D-glucopyranose
Authors: Marques Dinis Pinto Tiago Alexandre | Silva Marillia | Cunha Silvia | Oliveira-Campos Ana | Rodrigues Ligia | Hrdina Radim | Esteves Ana
Year: 2013
Type of publication: článek v odborném periodiku
Name of source: European Journal of Chemistry
Publisher name: European Journal of Chemistry
Place: Tucker
Page from-to: 64-69
Titles:
Language Name Abstract Keywords
cze Syntéza esterů odvozených z 2,3,4,6-tetra-O-acetyl-1-[4 -(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]-beta-D-glukopyranózy 2,3,4,6-Tetra-O-acetyl-1-[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]-beta-D-glukopyranosa byla připravena a použita pro reakci s několika kyselinami, buď komerčně dostupnými nebo se připravenými. Jednalo se a alifatické nebo aromatické kyseliny (deriváty fenyloctové a benzoové kyseliny), kyselinu palmitovou a chráněné aminokyseliny N-(benzyloxykarbonyl)glycin a N-(terc-butyloxykarbonyl)fenylalanin. Dvě další kyseliny, 2-(3-brompropoxy)benzoová kyselina a 2-(5-bromopentoxy)benzoová kyselina (analogy kyseliny salicylové byly syntetizovány), jejichž příprava je také popsána v této práci. Esterifikace byla provedena buď s N,N'-dicyklohexylkarbodiimid (DCC)/4-dimethylaminopyridinu (DMAP), nebo reakcí acyl chloridu s alkoholem v přítomnosti triethylaminu. Produkty byly izolovány v dobrých výtěžcích a plně charakterizovány obvyklými analytickými technikami. 1,2,3-triazoly glukopyranosy, glykokonjugáty, deriváty kyseliny benzoové, deriváty kyseliny octové deriváty kyseliny fenyloctové
eng Synthesis of esters derived from 2,3,4,6-tetra-O-acetyl-1-[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]-beta-D-glucopyranose 2,3,4,6-Tetra-O-acetyl-1-[4-(2-hydroxyethyl)- 1H-1,2,3-triazol-1-yl]-beta-D-glucopyranose was prepared and reacted with several acids, either commercially available or prepared. These included, aliphatic or aromatic acids (phenylacetic acid derivatives, benzoic derivatives), palmitic acid and the protected amino acids N-(benzyloxycarbonyl)glycine and N-(tert- butyloxycarbonyl)phenylalanine. Two other acids, 2-(3-bromopropoxy)benzoic acid and 2- (5-bromopentoxy)benzoic acid (analogues of salicylic acid were synthesized), whose preparation is also described in this work. The esterification was performed either with N,N'- dicyclohexylcarbodiimide (DCC)/4-dimethylaminopyridine (DMAP) or by reacting the acyl chlorides with the alcohol in the presence of triethylamine. The products were isolated in fair yields and fully characterized by the usual analytical techniques. 1,2,3-Triazoles Glucopyranose; Click chemistry Glycoconjugates; Benzoic acid derivatives; Phenyl acetic acid derivatives

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