2024-03-29T06:24:18Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/855432021-06-21T12:10:25Zcom_10261_33com_10261_5col_10261_286
1-exo-alkylidene-2,3-anhydrofuranoses: Valuable synthons in the preparation of furanose-based templates
Gómez, Ana M.
Pedregosa, A.
Uriel, Clara
Valverde, Serafín
López, J. Cristóbal
Highly functionalized 1-exo-alkylidene-2,3-anhydro-, and 1′-halo-1-exo-alkylidene-2,3-anhydrofuranoses can be prepared in four or five steps, respectively, from D-mannose. These compounds feature a variety of functionalities, including a double bond, an oxirane, an allylic oxirane and (in the case of the 1′-halo derivative) an alkenyl halide. The reactivity of each functionality in these derivatives has been explored, and the usefulness of these substrates has been demonstrated with the preparation of furanose-based carbohydrate templates with up to four sites of molecular diversity. A highly functionalized 1-exo-alkylidene-2,3-anhydro-furanose, available in four steps from D-mannose, is a useful substrate that can be transformed into a variety of furanose derivatives including compounds with up to four sites for diversity. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
2013-11-05T09:35:32Z
2013-11-05T09:35:32Z
2010
2013-11-05T09:35:33Z
artículo
European Journal of Organic Chemistry: 5619- 5632 (2010)
http://hdl.handle.net/10261/85543
10.1002/ejoc.201000612
eng
closedAccess
John Wiley & Sons