Tyvelose, synthesis

M. A. Probert, J. Zhang, and D. R. Bundle, Synthesis of a- and /blinked tyvelose epitopes of the Trichinella spiralis glycan 2-Acetamido-2-deoxy-3-0-(3, 6-dideoxy-D-arabmo-hexopyninosyl)-/)-D-galactopyranosides. Carbohydr. Res., 296 (1996) 149-170. 

E. H. Williams, W. A. Szarek, and J. K. N. Jones, Synthesis of paratose (3,6-dideoxy-D-rifw-hexose) and tyvelose (3,6-dideoxy-D-orahmo-hexose), Can. J. Chem. 49 796 (1971). 

C. Fouquey, J. Polonsky, and E. Lederer, Synthesis of three 3,6-dideoxyhexoses. Determination of the structure of the natural sugars tyvelose, ascarylose, and paratose, Bull. Soc. Chim. Fr. p. 803 (1959). 

Starting from 1,5-anhydro-2,3,4-tri-0-benzoyl-6-deoxy-D-ura >/ o-hex-1 -enitol (48), an unusual approach to the synthesis of disaccharides of serogroup A and D has applied the allylic rearrangement glycosylation procedure of Ferrier [127] to obtain an a-D-< rj//zTO-hex-2-enopyranosyl residue in the disaccharide 49a. Reduction of the 2-enopyranose double bond gave both the paratose (ribo) 49b and tyvelose (arabino) 49c products [28]. 

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