Lyxose L-, synthesis

Synthesis of Amino Sugars by Reduction of Hydrazine Derivatives. 2-Amino-2-deoxy-L-lyxose (L-Lyxosamine) Hydrochloride, D. Horton, M. L. Wolfrom, and A. Thompson,/. Org. Chem., 26, 5069-5074 (1961). 

L. Dubois and R. H. Dodd, Stereocontrolled synthesis of aziridine-2-lactones from D-ribose and D-lyxose, Tetrahedron, 49 (1993) 901-910. 

The synthesis of diol 56 from L-lyxose is reported. Compound 56 constitutes a subunit of the toxin erythroskyrine <96JCS(P1)1323>. 

The Wohl degradation214 of suitably acetylated aldononitriles was used for the synthesis of 5-deoxy-L-arabinose,216 5-deoxy-D-lyxose,2W and 5-deoxy-D-ribose.217 

Good diastereoselectivities were observed for the hetero Diels-Alder addition of homochiral 1,3-dienes with achiral acyl-nitroso dienophiles. An example is shown in Scheme 13.85 for the total synthesis of 4-amino-4,5-dideoxy-L-lyxose derivatives 300 and 301, potent inhibitors of a-L-fucosidase [160]. 

It is known that deamination of some readily available amino acids can be performed with nearly quantitative retention of configuration. Based on this conversion, Yamada and co-workers elaborated an ingenious synthesis of o-ribose and D-lyxose starting from L-glutamic acid. The preliminary communication of this work was reported in the first volume of Ais series.Now the full details have been published. In an extension of the application of the unsaturated intermediate (399) for the synthesis of other pentoses, all 2,3-anhydro derivatives (400-403) were prepared. LAH-Reduction of -D-ribo and o-D-lyxo epoxides (400 and 401) afforded, after acetylation, 3-deoxy-pentosides 404 and 405, whereas the same reaction conditions converted fi-D-lyxo a-D-ribo epoxides (402 and 403) into the corresponding 2-deoxy-derivatives (406 and 407). 

Walker et al. have described by tliis method a seven-step synthesis of 4-thio-2-deox-y-i3-eri f/7ro-pentosc (37) from 2-dcoxy-D-erir/ira-pentosc via dithioacetals 35 and 36, involving inversion at C-4 by Mitsunobu reaction and final cyclization of the dithioacetal, accompanied by further inversion at C-4. Secrist et al.- have synthesized 39 from the ribose derivative 38 using the same method. Similarly, Imbach et al. have prepared 1,4-dithio-D-ribofuranosides 39 from L-lyxose and from D-ribose,and 1,4-dithio-L-lyxofuranosides 40 from D-ribose. Mackenzie 

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