3-amino-2,3-dideoxy, synthesis

A. Grouiller, B. Nonga, M.-L. Navarro, P. Moliere, and H. Pacheco, Synthesis of amino-dideoxy-DL-pentopyranoses and their ureido derivatives, J. Carbohydr. Chem., 7 (1988) 507-524. 

Nucleophilic Displacement Reactions in Carbohydrates. Part XI. Reaction of Methyl 6-Deoxy-2,3-O-isopropylidene-4-O-methyl-sulphonyl-a-L-talopyranoside with Sodium Azide A Synthesis of L-Perosamine (4-Amino-4,6-dideoxy-L-mannose) Derivatives, J. S. Brimacombe, O. A. Ching, and M. Stacey, J. Chem. Soc. C, (1969) 1270-1274. 

Another application of diastereoselective nitro-aldol reactions catalyzed by Bu4NF-3H20 is demonstrated in a simple synthesis of l,4-dideoxy-l,4-imino-D-mannitol (DIM) and amino analogues (Eq. 3.85).134 The nitro-aldol reaction of nitro compounds bearing a-oxy or a-amino function with glyceraldehyde leads to nitrohexitols, which can be reduced to the corresponding amino compounds. Cyclization gives iminopolyols, as shown in Eq. 3.85. 

Following the discovery of the antiviral activity of the azidothymidine analog, and the activity of the 3 -azido-2 -dideoxyguanosine analog [262], the synthesis of a series of 2-amino-6-substituted-(3 azido-2, 3 -dideoxy-b-D-eryfhro-pento-furanosyl)purine analogs 196 was undertaken to explore the structure-activity relationships. 

The multi-enzyme system was recently utilized for the synthesis of dTDP-4-keto-6-deoxy-a-D-glucose 3 and dTDP-P-L-rhamnose 5 generating dlTP from dTMP by dTMP kinase and acetate kinase [66, 71]. Further combination with GerB, a dTDP-4-keto-6-deoxy-D-glucose aminotransferase, gave dTDP-4-amino-4,6-dideoxy-D-glucose [72]. 

L. Hough, A. A. E. Penglis, and A. C. Richardson, The synthesis of derivatives of 3-amino-2,3-dideoxy-2-fluoro-D-altrose, Carbohydr. Res., 83 (1980) 142-145. 

G. Legler and E. Jiilich, Synthesis of 5-amino-5-deoxy-D-mannopyranose and l,5-dideoxy-l,5-imino-D-mannitol, and inhibition of a- and P-D-mannosidases, Carbohydr. Res., 128 (1984) 61-72. 

An amidrazone (58) derived from 5-amino-5-deoxy-L-fuconolactam was found to inhibit a recombinant human a-L-fucosidase with a K -value of 820 nmol/1 [ 111 ]. A simple synthesis of 1,5-dideoxy-1,5-imino-D-arabinitol (59), previously prepared by Ganem et al. [49] as a potential maimosidase inhibitor, was applied to the affinity purification of a-L-fucosidase from bovine kidney by an improved method and the characterization of the enzyme thus obtained [112]. The relatively low affinity of this compound to the enzyme (Kj 2.2 pmol/1 at pH 7) compared to 1-deoxyfuconoJirimycin (51) turned out to be advantageous in terms of enzyme recovery and yield. Structurally related, suitably protected 5-amino-5-deoxy-D-arabinopyranose (60), was coupled with a N-acetyl-6-deoxy-6-thio-D-glucosaminide (61) to give a stable thioglycoside (62) [113]. 

The facile formation of the iodo compound, and the subsequent reduction with tributyltin hydride opens a new access to 2-amino-2,3-dideoxy-D-glucose (D-lividosamine) present in various aminoglycoside antibiotics [92], The same strategy been used in the synthesis of C-lO -C-l fragment of boromycin [93]. Displacement of the C-3 imidazylate ester of a 2-azido-2-deoxy-a-D-altropyranose derivative with benzoate occurred readily [94], compared with the corresponding tosylate [95],... 

Oppong KA, Hudlicky T, Yan F, York C, Nguyen BV (1999) Chemoenzymatic Enantio-divergent Synthesis of l,2-Dideoxy-2-amino-l-fluoro-a//o-inositol. Tetrahedron 55 2875... 

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