N-Gulose

Reeves has suggested that the spontaneous formation of 1,6-anhydro derivatives of idopyianose and altropyranose may be due to the conformational behavior of the aldoses his instability factors show that /3-Didose and /3-D-altrose will exist partly in the conformations favorable for closure of the 1,6-anhydro ring. This reasoning could lead to the further conclusions that D-talose, but probably not n-gulose, should fairly readily afford a 1,6-arihydro derivative of the pyranose form. 

If one considers the formulation of n-glucose phenylosazone (XXV), D-galactosephenylosazone (XXVI) and n-gulose phenylosazone (XXVII)... 

Phenylosotriazole n-Gulose phenylosotriazole. D-Idose phenylosotriazole. d-Sorbose phenylosotriazole C12H15N3O4 265.268 Cryst. (H2O). Mp 158.5-159°. [a]g +47... 

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). 

The compounds in this database retrieved as matches to the query substructure are n-gulose, n-glucose, n-xylose, 4-p-n-glucopyranosyl-p-n-glucopyranose, and n-sucrose. 

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