DL-Fucose

Verduyn, R. et al. Synthesis of Carba-P-DL-Fucose and Carba-fi-DL-Galactose from myo-Inositol. 3.1 1996(186]... 

Early studies of J. Adler have demonstrated that, in E. coli, the chemoattractants themselves are detected [6, 9] rather than their metabolic products. This conclusion was based on two types of observations. One was that mutant bacteria, which have lost the ability of metabolizing or transporting a chemical, can nevertheless be attracted to the chemical. The other type of observation was that nonmetabolizable analogs of metabolizable chemicals (e.g., D-fucose, a-methyl-DL-aspartate, or a-aminoisobutyrate— analogs of D-galactose, L-aspartate, or L-serine, respectively) attract bacteria. In contrast, some metabolizable chemicals... 

From Achiral Non-carbohydrates. — 3-Deoxy-3-guanidino-D-threose 48 equilibrates with 49. a transition state inhibitor for galactosidase. It was synthesized as shown in Scheme 12 from epoxide 47, which was obtained by porcine pancreatic lipase catalysed enantioselective esterification of the racemic epoxy-alcohol precursor. 6-Deoxy-L-talonolactone 50 was synthesized by an asymmetric aldol condensation - dihydroxylation sequence (Vol.24, p.lS2) in improved diastereoselectivity and was converted into 2-acetamido-2,6-dideoxy-L-fucose (shown as its furanose isomer 51 in Scheme 13), 3-acetamido-3,6Hlideoxy-L-idose and 5-acetamido-S,6-dideoxy-D-allose by S 2 displacements of triflate with azide ion. 4-Amino-4-deoxy-DL-erthrose 53 was obtained from the hetero-Diels-Alder adduct 52 by a sequence of reactions including cis-dihydroxylation (OSO4, NMNO) of the alkene moiety (Scheme 14). The synthesis of a racemic branched-chain lactam is covered in Chapter 16. 

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