(2R,3S,4R,5S)-5-aminohexane-1,2,3,4,6-pentol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 275 ml. of dry tetrahydrofuran and 275 ml. of dry dioxane was cooled to -5° and 12.88 ml. (9.35 g., 0.092 mole) of triethylamine, 8.74 ml. (9.96 g., 0.092 mole) of ethyl chloroformate and 19.23 g. (0.092 mole) of N-carbobenzyloxyglycine were added. The mixture was stirred for 15 min. at -5° and then a cold (0°-5°) solution of 16.65 g. (0.092 mole) of 2-amino-2-deoxy-D-glucitol in 40 ml. of water was added in one portion. The cooling bath was removed and the mixture was allowed to stir at ambient temperature for four hours. The solvent was evaporated in vacuum at 30°-40° and the residue was stirred overnight with 500 ml. of ethanol. Filtration furnished 30 g. of a solid. The solid was recrystallized from 700 ml. of methanol to give 21 g. of product. Tlc shows the product to be pure (silica gel plate--benzene/methyl ketone/88% formic acid 60:25:25--methanolic sulfuric acid development). A mixture of 275 ml a cold (0°-5°) solution of 16.65 g The cooling bath was removed to stir at ambient temperature for four hours The solvent was evaporated in vacuum at 30°-40° the residue was stirred overnight with 500 ml Filtration furnished 30 g The solid was recrystallized from 700 ml of methanol to give 21 g