Synthesis, Table of Contents PSP © Georg Thieme Verlag Stuttgart · New York Preparation of Butane-1,2-diacetal-protected l-Glyceraldehyde from d-Mannitol Steven V. Ley*, Patrick MichelDepartment of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UKe-Mail: svl1000@cam.ac.uk.; Recommend Article Abstract Buy Article All articles of this category Abstract (2S, 5R, 6R)-5,6-Dimethoxy-5,6-dimethyl-[1,4]dioxane-2-carbaldehyde (5) represents a important stable alternative to glyceraldehyde acetonide. Its synthesis on a large scale from inexpensive d-mannitol is described together with other related building blocks. Key words 1,2-diacetals - glyceraldehydes - glyceric esters - alkylation Full Text References References 1a Baer E. Fisher HOL. J. Bio. Chem. 1939, 128: 463 1b Jurczak J. Pikul S. Bauer S. Tetrahedron 1986, 42: 447 2a Hertel LW. Grossman CS. Kroin JS. Synth. Commun. 1991, 21: 151 2b Hubschwerlen C. Specklin J.-L. Higelin J. Org. Synth. 1995, 72: 1 2c Schmid CR. Bryant JD. Org. Synth. 1995, 72: 6 3a Ley SV. Woods M. Zanotti-Gerosa A. Synthesis 1992, 52 3b Ley SV. Downham R. Edwards PJ. Innes JE. Woods M. Contemp. Org. Synth. 1995, 2: 365 3c Jäeger V. Wehner V. Angew. Chem. Int. Ed. Engl. 1989, 28: 469 For some recent examples see: 4a Diez E. Dixon DJ. Ley SV. Angew. Chem. Int. Ed. 2001, 40: 2906 4b Dixon DJ. Ley SV. Polara A. Sheppard T. Org. Lett. 2001, 3: 3749 4c Dixon DJ. Ley SV. Rodriguez F. Org. Lett. 2001, 3: 3753 4d Dixon DJ. Ley SV. Rodriguez F. Angew. Chem. Int. Ed. 2001, 40: 4763 4e Ley SV. Michel P. Synlett 2001, 1793 4f Kiyota H. Dixon DJ. Luscombe CK. Hettstedt S. Ley SV. Org. Lett. 2002, 4: 3223 4g Dixon DJ. Guarna A. Ley SV. Polara A. Rodriguez F. Synthesis 2002, 1973 4h Dixon DJ. Harding CI. Ley SV. Chem. Commun. 2003, 468 4i Diez E. Dixon DJ. Ley SV. Polara A. Rodriguez F. Synlett 2003, 1186 4j For a review see: Ley SV. Baeschlin DK. Dixon DJ. Foster AC. Ince SJ. Priepke HWM. Reynolds DJ. Chem. Rev. 2001, 101: 53 5a Michel P. Ley SV. Angew. Chem. Int. Ed. 2002, 41: 3898 5b Michel P. Ley SV. Synthesis 2003, 1598 6a Berens U. Leckel D. Oepen SC. J. Org. Chem. 1995, 60: 8204 6b Hense A. Ley SV. Osborn HMI. Owen DR. Poisson J.-F. Warriner SL. Wesson KE. J. Chem. Soc., Perkin Trans. 1 1997, 2023 7 Lichtenthaler FW. Jarglis P. Lorenz K. Synthesis 1988, 790 8 Ley, S.V.; Michel, P.; Trapella, C. Org. Lett., in press.
