4-Deoxy-Zyxo-hexose

On reduction with sodium borohydride, product II yielded a pair of radioactive products that were tentatively identified as 2-deoxy-L-Zyxo-hexose and 2,6-dideoxy-L-arafeino-hexose. This result, together with the chromatographic properties of II, and its reaction on chromatograms with vanillin-perchloric acid to give a blue color, are consistent with the structure of 2,6-dideoxy-L-Zyxo-hexos-4-ulose (20) for II. This structure is also consistent with the concept that II (20) is, very probably, the precursor of III (19). 

Dideoxy-3-0-methyl-Zyxo-hexose 6-Deoxy-3-0-methyl-D-galactose... 

Brimacombe and How reduced methyl 3,4-0-isopropylidene-2,6-di-O-p-tolylsulfonyl-a-D-galactopyranoside with lithium aluminum hydride in tetrahydrofuran, to provide methyl 3,4-O-isopropylidene-2-0-p-tolylsulfonyl-a-D-fucopyranoside in 54% yield. In later reductions of closely related compounds, the solvent chosen was ether-benzene methyl 3-0-benzyl-2-deoxy-6-0-p-tolylsulfonyl-a-D-Ii/xo-hexopyranoside afforded the corresponding 6-deoxy compound which, on methylation, debenzylation, and acid hydrolysis, gave 2,6-dideoxy-4-O-methyl-D-Zi/Jco-hexose (chromose A). An improved synthesis of this sugar involved the reduction, in ether—benzene (1 1), ofmethyl 2-deoxy-4-0-methyl-3,6-di-0-p-tolylsulfonyl-a-D-/i/xo-hexopyranoside to methyl 2,6-dideoxy-4-0-methyl-a-D-Z /xo-hexopy-ranoside in 25% yield a synthesis of 3-0-acetyl-2,6-dideoxy-D-Z /xo-hexose (chromose D) was effected by way of reduction in ether-benzene (2 1) of methyl 2-deoxy-6-0-p-tolylsulfonyl-a-D-Zyxo-hexo-pyranoside to the corresponding 6-deoxy compound in 27% yield, followed by partial acetylation and acid hydrolysis. 

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