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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)

Wednesday, December 11, 2019

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