Glucose 2-deoxy-2-ureido

Related 2-deoxy-2-ureido-D-glucose derivatives can be obtained by direct reaction of phenyl isocyanate or silver isocyanate with LXXXIII, the former giving LXXXVIII, whereas the latter affords the free 2-ureido derivative LXXXIX.164,188 This reaction contrasts with the behavior of LXXXIII with isothiocyanates, which react at Cl (see p. 244). 

Deoxy-2-ureido derivatives of D-glucose have been known for many years,189,190 but only recently have their properties been studied in detail. The acetate esters show a marked resistance to catalytic de-O-acetylation with sodium methoxide, only the 1-O-acetyl group being removed.164 This behavior resembles that of 1,3,4,6-tetra-0-acetyl-2-deoxy-2- iV,iV-bis[2-... 

Syntheses of amino-sugar C-glycosides and dihydroxy-amino acids from 2-amino-2-deoxy-D-glucose are covered in Chapters 3 and 24, respectively, formation of 1,4-pyridazines by dimerization of 2-amino-sugars is covered in Chapter 10, and H-n.m.r. studies of 2-deoxy-2-ureido-p-glucosides in Chapter 21. 

Reaction of 2-amino-2-deoxy-D-glucose hydrochloride with potassium qranate yields a mixture from which, after acetylation, the fused urea derivative (20) and the heterocycle (21) were isolated 2-deoxy-2-ureido-D-glucose is postulated as an intermediate in the formation of both products. Reaction of 2-amino-2-deoxy-D-g/ycere>-L-g/Mco-heptose with cyanamide gave the fused guanidine salt (22) acetylation of the crude reaction product provided both the fused urea derivative (23) and the heterocycle (24). ... 

---