3 - Amino-3 -deoxysugars synthesis

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. 

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. ... 

D. Lafont, A. Wollny, and P. Boullanger, Synthesis of 6-amino-l,6-anhydro-6-deoxysugar derivatives, Carbohydr. Res., 310 (1998) 9-16. 

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