Synthesis of alkyl 4,6-di-o-acetyl-2,3-dideoxy-α-d-threo-hex-2- enopyranosides from 3,4,6-tri-o-acetyl-1,5-anhydro-2-deoxy- d-lyxo-hex-1-enitol (3,4,6-tri-o-acetyl-d-galactal) |
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Authors: | Grzegorz Grynkiewicz Waldemar Priebe Aleksander Zamojski |
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Institution: | Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warszawa Poland |
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Abstract: | 3,4,6-Tri-O-acetyl-d-galactal, on treatment in 1,2-dichloroethane with alcohols and stannic chloride as catalyst, readily undergoes allylic rearrangement-substitution, forming alkyl 4,6-di-O-acetyl-2,3-dideoxy-α-d-threo-hex-2-enopyranosides in yields of 43-92%. Alkyl 3,4,6-tri-O-acetyl-2-deoxy-αβ-d-lyxo-hexopyranosides are formed as side-products in yields of 2-14 %. Stannic chloride-catalysis is also useful in allylic rearrangement of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-d-arabino- hex-l-enitol (3,4,6-tri-O-acetyl-d-glucal) which, with methanol or ethanol, affords the corresponding alkyl 4,6-di-O-acetyl-2,3-dideoxy-α-d-erythro-hex-2-enopyranosides in yields of 83 and 94%. |
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