Partially protected D-glucopyranosyl isothiocyanates. Synthesis and transformations into thiourea and heterocyclic derivatives.
1992; Elsevier BV; Volume: 48; Issue: 31 Linguagem: Inglês
10.1016/s0040-4020(01)88231-4
ISSN1464-5416
AutoresJosé M. Fuentes, Wenceslao Moreda, Carmen Ortiz, Inmaculada Robina, Colin L. Welsh,
Tópico(s)Polyamine Metabolism and Applications
ResumoThe syntheses of 2,3,4-tri-O-acetyl(benzoyl)-β-D-glucopyranosyl isothiocyanates (3, 4) from the corresponding acylated N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine are described. Reactions of 3 and 4 with phenacylamine hydrochloride yielded N-phenacyl-N′-(2,3,4-tri-O-acyl-β-D-glucopyranosyl)thioureas (6, 7) whereas treatments of the same compounds with aminoacetone hydrochloride gave the N-nucleoside analogues 5-methyl-1-(2′,3′,4′-tri-O-acyl-β-D-glucopyranosyl)-4-imidazoline-2-thiones (8, 9). The partially protected N-(2-thiazoline-2-yl)-β-D-glucopyranosylamine (10) and the thioureylenedisaccharide II were prepared from 4 and 2-chloroethylamine hydrochloride under different reaction conditions.
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