Synthesis of the Bis-Tetrahydropyrano[2,3-b:2’,3’-e] Piperazine Ring System: A New Tricyclic Heterocycle from D-Glucosamine

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https://orcid.org/0000-0003-2219-5833

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ENG

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2-Amino-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose was transformed into its bis(tetrahydropyranyl)piperazine dimer (4) by reaction with 1,1′-thionyldiimidazole or 1,1′-sulfonyldiimidazole. This dimeric form of glucosamine is the first representative of this previously unknown heterocyclic ring system.

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Journal of Carbohydrate Chemistry, 15, 581-590
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Synthesis of the Bis-Tetrahydropyrano[2,3-b:2’,3’-e] Piperazine Ring System: A New Tricyclic Heterocycle from D-Glucosamine, R.J. Kerns, T. E. Toida, R.J. Linhardt, Journal of Carbohydrate Chemistry, 15, 581-590, 1996.

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7328303

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