Tetrahedron p. 5797 - 5810 (1991)
Update date:2022-08-04
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Pradera
Robina
The syntheses of 3,4,6-tri-O-acetyl-2-deoxy-α and β-D-arabino(D-lyxo)hexopyranosyl isothiocyanates (2, 3, 6, 7) and 4, 6-di-O-acetyl-3-bromo-2,3-dideoxy-β-D-arabinohexopyranosyl isothiocyanate (5) are reported. Treatments of 2,3,6, and 7 with phenacylamine hydrochloride and of 2 with aminoacetone hydrochloride gave the corresponding N-phenacyl (acetylmethyl-N'-(2-deoxyglycosyl)-thioureas (8-12). The N-nucleoside analogues 5-methyl-1-(3',4',6'-tri-O-acetyl-2'-deoxy-α-D- arabinohexopyranosyl)-4-imidazoline-2-thione (13) was obtained by cyclodehydration of the thiourea 12.
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Doi:10.1016/S0040-4039(00)79878-9
(1991)Doi:10.1016/j.bmcl.2010.03.077
(2010)Doi:10.1080/10286020.2012.699961
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(2017)Doi:10.1016/j.molcata.2012.01.022
(2012)Doi:10.1016/0022-2860(91)85055-8
(1991)
