Selective mono-O-alkylation (protection) of carbohydrates catalyzed by stannylene acetals

Selective mono-O-alkylation (protection) of carbohydrates catalyzed by stannylene acetals

Silva, Angelo Amaro T. da; Dias, Tamires de O. B.; Simas, Alessandro B. C.

Abstract:

Carbohydrates and their derivatives play important roles in nature. The use of such natural materials in the synthesis of complex oligomers, analogues, or chiral building blocks (in total synthesis) depends on efficient methodologies for selective protection. Previously, we had demonstrated that selective Oalkylation of polyols may be catalyzed by stannylenes. Thus, di-O-benzylation of D-mannitol derivative 1 was carried out efficiently with low load of the tin reagent (only ~15 mol% of depolymerized Bu2SnO was used) (Scheme 1).

Carbohydrates and their derivatives play important roles in nature. The use of such natural materials in the synthesis of complex oligomers, analogues, or chiral building blocks (in total synthesis) depends on efficient methodologies for selective protection. Previously, we had demonstrated that selective Oalkylation of polyols may be catalyzed by stannylenes. Thus, di-O-benzylation of D-mannitol derivative 1 was carried out efficiently with low load of the tin reagent (only ~15 mol% of depolymerized Bu2SnO was used) (Scheme 1).

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DOI: 10.5151/chempro-14bmos-R0039-1

Referências bibliográficas

• [1] 1 Bertozzi, C. R. Science 2001, 291, 2357-2364.
• [2] 2 Stallforth, P.; Lepenies, B.; Adibekian, A.; Seeberger, P. J. Med. Chem. 2009, 52, 5561-5577.
• [3] 3 Wang, C.; Lee, J.; Luo, S.; Kulkarni, S.; Huang, Y.; Lee, C.; Chang, K.; Hung, S. Nature 2007, 446, 896-899 and cited refs..
• [4] 4 Simas, A. B.; Silva, A. A. D.; Filho, T. J. D. S.; Barroso, P. T. Tetrahedron Letters 2009, 50, 2744-2746 and cited refs..

Como citar:

Silva, Angelo Amaro T. da; Dias, Tamires de O. B.; Simas, Alessandro B. C.; "Selective mono-O-alkylation (protection) of carbohydrates catalyzed by stannylene acetals", p-39-39. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0039-1