1,5-Anhydro-D-Fructose – Efficient Synthesis and Chemical Uses

1,5-Anhydro-D-fructose (AF) is a valuable chiral building block for organic synthesis.[1] However, the antioxidant and antimicrobial properties of AF are equally important.[1] Due to these interesting properties AF is heavily patented for the use in pharmaceuticals, foods and cosmetics. However, the preparation of AF, as well as 1,5- and 1,4-anhydroketoses in general, is still a challenging task. An a-1,4-glycan lyase which degrades starch into AF has been identified, cloned and expressed in bacteria [2] but this fact does not yet give access to AF on a commercial basis. Neither are efficient chemical methods available despite the fact that the first low-yielding procedure by Lichtenthaler et al. was already described in 1980.[3] In this presentation we will show new and efficient chemical methods employing easily available and cheap starting materials for the synthesis of 1,5- and 1,4-anhydroketoses as well as for derivatives and analogues thereof. The potential of AF will be highlighted as will be the use of AF as a chiral building block for the preparation of other interesting compounds with biological activities such as, for example, Deoxymannojirimycin (DMJ). [1] S.M. Andersen, I. Lundt, J. Marcussen, S. Yu, Carbohydr. Res.,337, 873 (2002). [2] K. Bojsen, S.Yu, Shukun, K. M. Kragh, J. Marcussen, Biochimica et Biophysica Acta , 1430, 396, (1999). [3] F.W. Lichtenthaler, E.S.H. El Ashry, V.H. Göckel, Tetrahedron Lett. 21, 1429 (1980).