Preparative synthesis of C-(alpha-D-glucopyranosyl)-alkenes and -alkadienes: Diels-Alder reaction.
The reaction of 2,3,4,6-tetra-O-benzyl-1-O-(p-nitrobenzoyl)-alpha-D-glucopyranose with (E)-penta-2,4-dienyltrimethylsilane and boron trifluoride etherate in acetonitrile afforded stereoselectively (E)-5-(tetra-O-benzyl-alpha-D-glucopyranosyl)-1,3-pentadiene in good yield. The readily available penta-O-benzoyl-alpha-D-glucopyranose reacted with allyltrimethylsilane in the presence of boron trifluoride etherate in acetonitrile to give 3-(tetra-O-benzoyl-alpha-D-glucopyranosyl)-1-propene and its beta anomer in yields of 60% and 2.3%, respectively. Diels-Alder cycloaddition of maleic anhydride to diene 1 afforded the adduct cis,cis-3-(tetra-O-benzyl-alpha-D-glucopyranosylmethyl)cyclohex -4-ene- 1,2-dicarboxylic anhydride in high yield.
de Gracia Garcia Martin
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Department of Chemistry, Ohio State University, Columbus 43210.
Horton
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D000466:Alkadienes / Q000138:chemical synthesis*; D000475:Alkenes / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D055598:Chemical Phenomena; D002621:Chemistry; D005960:Glucosides / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000466:Alkadienes; D000475:Alkenes; D005960:Glucosides; D006027:Glycosides; C061819:5-(tetra-O-benzyl-alpha-glucopyranosyl)-1,3-pentadiene; C061820:3-(tetra-O-benzoyl-alpha-glucopyranosyl)-1-propene