Dehydration of D-mannitol: building block for C-nucleoside synthesis

Dehydration of D-mannitol: building block for C-nucleoside synthesis

Siqueira, Edmilson Clarindo de; Y.Nazarenko, Alexander; Doboszewski, Bogdan

Abstract:

D-Mannitol 1 is a convenient starting material for organic synthesis because of the homotopic relation between the upper and the lower part of the molecule. For this reason dehydration of 1 via 2-5 hydroxyl groups yields one product only, i.e. 2,5,- anhydro-D-glucitol 2. Our interest in 2 and its derivative 5 stems from a possibility of application of the latter for C-nucleoside synthesis. Acid catalyzed dehydration of 1 was performed followed by some manipulations, and permitted isolation of the 2,5- anhydro-4,6-di-O-benzyl-D-glucitol 5, together with 2,6-anhydro-1,3-di-O-benzyl-D-mannitol 7 (or 1,5- anhydro-4,6-di-O-benzyl-D-mannitol due to a symmetry of 1). A structure of 7 was confirmed by xray analysis.

D-Mannitol 1 is a convenient starting material for organic synthesis because of the homotopic relation between the upper and the lower part of the molecule. For this reason dehydration of 1 via 2-5 hydroxyl groups yields one product only, i.e. 2,5,- anhydro-D-glucitol 2. Our interest in 2 and its derivative 5 stems from a possibility of application of the latter for C-nucleoside synthesis. Acid catalyzed dehydration of 1 was performed followed by some manipulations, and permitted isolation of the 2,5- anhydro-4,6-di-O-benzyl-D-glucitol 5, together with 2,6-anhydro-1,3-di-O-benzyl-D-mannitol 7 (or 1,5- anhydro-4,6-di-O-benzyl-D-mannitol due to a symmetry of 1). A structure of 7 was confirmed by xray analysis.

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DOI: 10.5151/chempro-14bmos-R0023-2

Referências bibliográficas

• [1] 1 Hartman, L. Separation of hexitans (anhydrohexitols). 1970, US Patent 3,484,459.
• [2] 2 Doboszewski, B.; Siqueira, E.C. de. Synth.Commun. 2010, 40, 744.
• [3] 3 Harwood, L.M. Aldrichim. Acta, 1985, 18, 25.

Como citar:

Siqueira, Edmilson Clarindo de; Y.Nazarenko, Alexander; Doboszewski, Bogdan; "Dehydration of D-mannitol: building block for C-nucleoside synthesis", p-23-23. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0023-2