Talopyranose 4-amino-1,6-anhydro-4-deoxy

The deamination of methyl 3-amino-3-deoxy-/3-D-altropyranoside was studied in 1934, but the products were not fully characterized.14411 The syrupy product was converted into a methylated derivative that had an elemental analysis corresponding to that calculated for a methyl tetramethylhexoside. The conditions used for methyl-ation would have opened an epoxide ring. Methyl 2,3-anhydro-4,6-0-benzylidene-a-D-mannopyranoside precipitated quantitatively from solution when the corresponding 3-amino-3-deoxyaltroside derivative was deaminated in aqueous medium.145 Epoxide formation was likewise reported to be quantitative in the deamination of the analogous 2-amino-2-deoxyaltroside.83 145 On deamination, 4-amino-l,6-anhydro-4-deoxy-/3-D-mannopyranose also gave an epoxide, namely, 1,6 2,3-dianhydro-/3-D-talopyranose, in unspecified yield.146... 

A. K. Chatterjee, D. Horton, J. S. Jewell, and K. D. Philips, Synthesis of 1,6-anhydro derivatives of 2-amino-2-deoxy-jS-D-talopyranose and 4-amino-4-dcoxy-/i-n-talopyranose, Carbohydr. Res., 7 (1968) 173-179. 

A mixture of l,6-anhydro-3,4-0-isopropylidene-y -D-/yxo-hexopyranos-2-ylose oxime, PtOa, coned. HCl, and 95%-ethanol hydrogenated 16 hrs. at room temp, and 50 p.s.i. -> 2-amino-l,6-anhydro-2-deoxy-/ -D-talopyranose hydrochloride. Y ca. 100%. A. K. Chatterjee et al., Carbohydrate Res. 7, 173 (1968). 

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