Idopyranose 6-amino-1,6-anhydro-6-deoxy

Another route to 5-amino-5-deoxy-L-idose proceeds from 5-(benzyl-amino)-5-deoxy-l,2-0-isopropylidene-R-L-idurononitrile (56), which is readily obtainable from 1,2-O-isopropylidene-a-D-xj/lo-pentodialdo-1,4-furanose (13) by reaction with benzylamine and hydrogen cy-anide. Partial hydrogenation of the nitrile 56 by the Kuhn procedure, in acid solution, leads to the hexodialdose (57), which is reduced with sodium borohydride to 5-amino-5-deoxy-l,2-0-isopro-pylidene-jS-L-idofuranose. From this compound, tbe acyclic bisulfite adduct (58) is obtained by reaction with sulfiirous acid. Treatment of 58 with barium hydroxide gives crystalline 5-amino-l,6-anhydro-5-deoxy-jS-L-idopyranose (60) in almost quantitative yield. The equilibrium between the pyranose form (61) and its 1,6-anhydride (60) lies far on the side of Ae bicyclic form (60). The equilibrium can be evaluated from the optical rotation of the solution obtained by treat-... 

Methyl 2-acetamido-5,6-anhydro-2-deoxy-0 -L-idofuranoside (33) has been synthesized from 2-acetamido-2-deoxy-D-glucose and has been employed in the preparation of 2-acetamido-5-amino-2,5-dideoxy-D-glucopyranose as the sulphur dioxide adduct (34) (Scheme 7). Similarly the corresponding idopyranose was prepared in an analogous manner. ... 

Amino-l,6-anhydro-2-deoxyglucose p-D-Pyranose-/orm, A-132 5-Amino-l,6-anhydro-5-deoxy-p-L-idopyranose, A-293... 

Acetamido-5-amino-2,5-dideoxy-L-idopyranose, D-441 2-Acetamido-4-amino-2,4,6-trideoxy-D-galactose, D-473 4-Acetamido-2-amino-2,4,6-trideoxy-D-glucose, D-474 2-Acetamido-l,5-anhydro-3-0-benzyl-4,6-0-benzylidene-2-deoxy-D-... 

Amino-l,6-anhydro-5-deoxyaItrose p-L-Furanose-ybrm, A-124 5-Amino-2,6-anhydro-5-deoxyiditoI i>-form N-Ac, A-138 5-Amino-2,6-anhydro-5-deoxyiditoI r>-form, A-138 5-Amino-1,6-anhydro-5-deoxy-p-L-idopyranose, A-293 5-Amino-3-0-benzyl-5-deoxy-l,2-0-isopropyIidene-a-D-xyIofuranose, A-358... 

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