3- Amino-3 -deoxysugars

For the synthesis of glycans containing 2-amino-2-deoxysugars, the regioselective azidophenylselenation of glycals is popular [524—528]. This methodology follows on from the classic azidonitration work of Lemieux and Ratdiffe, first reported in the... 

The Synthesis of 2-Amino-2-deoxysugars from Acetylated Glycals, R. U. Lemieux and T. L. Nagabhushan, Tetrahedron Lett., No. 26 (1965) 2143-2147. 

The 3-amino-4,7-dihydroxy-coumarin moiety is a core unit of this family of compounds. The amino group of coumarin scaffold is further decorated with derivatives of pyrrole or benzoic acid moieties. Also, branched deoxysugar 5-C-methyl-L-rhamnose (noviose) is installed onto one of the hydroxyls of the coumarin. Clorobiocin 67 and novobiocin 68 can be considered prototypical aminocoumarins. These molecules are potent inhibitors of bacterial gyrase and topo-isomerase IV and 68 is used to treat human infections. Several works also showed that analogs of 68, in combination with other drugs, can improve the chemotherapy of certain tumors [121]. 

Scheme 9. 5-Deoxysugars The 5-amino-5-deoxysugars (piperidinoses) nojirimycin (17), 1-de-oxynojirimycin (18), mannojirimycin (19) and galactostatin (20). The tetrahydropyrrol moiety of bulgecin A (21) and the allosamizoline unit 22 of allosamidine (23can also be considered as 5-deoxysugars. The derivation of 22 from the pool has already been proven...

SCHEME 6.62 Cyanohydrin reactions can generate 2-amino-2-deoxysugars. 

SCHEME 6.81 2-Amino-2-deoxysugars can be epimerized at C-2 under basic conditions. 

Glycoconjugates Antitumor and antimicrobial drugs Deoxysugars Molecular recognition Antibiotic resistance Antiadhesives Sugar amino acids Functional glycoconjugates... 

Photooxidation rates of propan-2-ol in aqueous Ti02 suspensions are reported to be increased by ultrasound radiation, an observation which has been rationalised in terms of mass transport of the substrate and activation of the solid catalyst. The value of the newly described photochemical rearrangement of 2-phenylthio-l,3-cyclohexanediols such as (69) to deoxysugars (70) which are in equilibrium with the closed form (71) has been illustrated by its application to the synthesis of (+)-m-rose oxide (72), and the same authors have also described the regioselective photorearrangement of 2-phenylthio-3-aminocyclohexanols (73) to deoxyazasugars (74) this has proved to be useful in the synthesis of various piperidines (75), amino-sulfones, -sulfoxides and -acids. Hydroxy(alkoxy)methyl radicals have been generated by photo-induced electron transfer. ... 

---