6-Deoxy-D-gulose

Occurrence. 6-Deoxy-D-gulose (36) occurs in steroidal glycosides,160 for example, from the sap of the upas tree, Antiaris toxicaria,169 from the walldower, Cheiranthus cheiri,170 and from Digitalis canariensis var. isabelliana.162 It has also been described in the lipopolysaccharide O-antigen of Yersinia enterocolitica serotype 0 8.171... 

Preparation. 6-Deoxy-D-gulose was originally prepared by the cyanohydrin synthesis from 5-deoxy-D-xylose. A simple preparation of 6-deoxy-D-gulose from D-gulono-1,4-lactone has been described.172... 

D-aIIomethyIose(20)L-aItromethylose(21) D-antiarose (22) D-digitalose (23) L-talomethylose (29) 6-deoxy-D-aIIose 6-deoxy-L-aItrose 6-deoxy-D-gulose 6-deoxy-3-0-methyI- 6-droxy-L-taIose Qll D-galactose... 

A number of 6-deoxyhexoses also are widespread in plants, but these compounds are especially common in cardiac glycosides (Courtois and Percheron, 1970). These sugars are formed from the corresponding hydroxylated monosaccharides (Luckner, 1990). Among the 6-deoxyhexoses are L-acofriose (6-deoxy-3-0-methyl-L-mannose) (18), l-acovenose (6-deoxy-3-6>-methyl-L-talose) (19), o-allometh-ylose (6-deoxy-D-allose) (20), L-altromethylose (6-deoxy-L-altrose) (21), D-antiarose (6-deoxy-o-gulose) (22), D-boivi-nose (2,6-dideoxy-D-xy/o-hexose) (17), D-cymarose (2,6-di-... 

A method of more general application depends on the reduction of iodo derivatives in which the iodine has replaced the hydroxyl of a primary alcoholic group. These are easily obtained by treatment of the tosyl derivatives with sodium iodide in acetone solution (sealed tube) or in refluxing acetonyl-acetone 228) or acetic anhydride 229). The reduction is often carried out by catalytic methods. The 5-deoxy-n-xylose is synthesized from D-xylose by this method, and by application of the cyanohydrin synthesis 6-deoxy-n-gulose is prepared 230). 

C-Labelled D-glucose was incorporated into the 2-amino-2-deoxy-D-gulose residue present in racemomycin A, a streptothricin antibiotic. C N.m.r. measurements have been used to investigate the incorporation of D-[6- C]glucose into spectinomycin hydrate (390) by growing cultures of S. spectabilis. The... 

A. C. Richardson and H. O. L. Fischer, Cyclization of dialdehydes with nitromethane, Part VI. Preparation of 3- amino-1,6-anhydro-3-deoxy-p-D-gulose, -P-D-altrose and -p-D-idose derivatives and their characterization by means of inversion of mesyloxy groups,./. Am. Chem. Soc., 83 (1961) 1132-1139. 

Deoxy-3-C-methyl-2,3,4-tri-0-methyl-L-mannose (17) 6-Deoxy-3-C-methyl-D-gulose (18)... 

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