Conversion of 2-amino-2-deoxy-D-glucose diethyl dithioacetal hydrochloride into 2-s-ethyl-2-thio-D-glucose
1968; Elsevier BV; Volume: 6; Issue: 3 Linguagem: Inglês
10.1016/s0008-6215(00)81451-2
ISSN1873-426X
AutoresA.E. El Ashmawy, Derek Horton, Ligaya G. Magbanua, J. M. J. TRONCHET,
Tópico(s)Biopolymer Synthesis and Applications
ResumoTreatment of 2-amino-2-deoxy-D-glucose diethyl dithioacetal hydrochloride (1) with nitrous acid in aqueous hydrochloric acid gives 2-S-ethyl-2-thio-D-glucose (2) as the principal product, and an anhydro-D-hexose diethyl dithioacetal is not formed. Substance 2 was characterized by conversion into the phenylhydrazone (3) and further into D-arabino-hexulose phenylosazone (6); n.m.r. spectroscopy confirmed that 2 was an aldose having the D-gluco configuration. Acetylation of 2 gave the anomeric pyranose tetraacetates (4 and 5), and the n.m.r. spectrum of the β-D tetraacetate (4) further confirmed the structure assigned to 2. Nitrous acid in aqueous acetic acid converted 1 into a mixture of 2 and an anhydro-D-hexose diethyl dithioacetal.
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