Synthesis and oxidation of thioglicosides underlain by neomenthanethiol,D-glucose,and D-fructose |
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Authors: | S V Pestova E S Izmest’ev S A Rubtsova A V Kuchin |
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Institution: | 1. Institute of Chemistry, Komi Scientific Center, Ural Branch, Russian Academy of Sciences, Pervomaiskaya ul. 48, Syktyvkar, 167982, Russia
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Abstract: | Synthesis of sulfides proceeding from neomenthanethiol, 1,2-O-isopropylidene-α-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose was performed to get 65 and 54% yield respectively. Oxidation of the sulfides afforded diastereomeric sulfoxides in the yields from 40 to 53%, and diastereomeric excess (de) up to 36%. After removing the isopropylidene protection from 1-deoxy-1-(1S,2S,5R)-2-isopropyl-5-methylcyclohexylsulfanyl]-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose a water-soluble sulfide was obtained. |
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