ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Diethyl derivatives of 2,3:4,5-di-O-isopropylidene-D-galactose

J. Trúchly, Š. Bauer, and D. Šikl

Slovak Academy of Sciences, Bratislava

Abstract: The di-Et dithioacetal (I) of 2,3:4,5-di-O-isopropylidene-D-galactose can be substituted in the 6 position. Di-Et dithioacetal (II) of 2,3: 4,5-di-O-isopropylidene-6-O-methyl-D-galactose, [α]25D -55° (c 1, CHCl₃), was prepd. by heating I with NaOH and Me₂SO₄. Hydrolysis of II with concd. HCl gave diethyl dithioacetal of 6-O-methyl-D-galactose, m. 134° [α]25D 6.2° (c 1, MeOH). By the reaction of I with Ac₂O and pyridine at room temp., di-Et dithioacetal of 6-O-acetyl-2,3:4,5-di-O-isopropylidene-D-galactose, [α]25D -44.8° (c 1, CHCl₃), was prepd. By the reaction of I with pyridine and Ph₃CCl at room temp., di-Et dithioacetal of 2,3:4,5-di-O-isopropylidene-6-O-trityl-D-galactose, [α]24D -26.6° (c 1.5, CHCl₃), was prepd. I was isolated on preparative chromatography in CHCl₃ on a thin layer of Al₂O₃ as a sirup with Rf 0.64 and [α]23D -53.2° (c 1, CHCl₃).

Full paper in Portable Document Format: 1911a860.pdf (in Slovak)

Chemical Papers 19 (11) 860–863 (1965)