The reaction of 5,6-anhydro-1,2-O-isopropylidene-alpha-D-glucofuranose (I) with monobenzylether of hydroquinone (II) by means of pyridine at 120 C gives 1,2-O-isopropylidene-6-O-(4-benzyloxyphenyl)-alpha-D-glucose (III), which is hydrolized with acetic acid yielding 6-O-(4-benzyloxyphenyl)-alpha-D-glucose (IV). The cleavage of (IV) with NaIO4 in methanol - acetic acid, followed by reduction of the resulting product with NaBH4 in methanol affords 1-(4-benzyloxyphenoxy)-2S-3-dihydroxypropane (V), which is monotosylated with tosyl chloride in pyridine giving the tosyl derivative (VI). The reaction of (VI) with isopropylamine (VII) in hot ethanol affords (S)-3-isopropylamino-1-(4-benzyloxyphenoxy)-2-propanol (VIII), which is finally debenzylated by reduction with H2 over Pd/C in ethanol.

The reaction of 5,6-anhydro-1,2-O-isopropylidene-alpha-D-glucofuranose (I) with monobenzylether of hydroquinone (II) by means of pyridine at 120 C gives 1,2-O-isopropylidene-6-O-(4-benzyloxyphenyl)-alpha-D-glucose (III), which is hydrolized with acetic acid yielding 6-O-(4-benzyloxyphenyl)-alpha-D-glucose (IV). The cleavage of (IV) with NaIO4 in methanol - acetic acid, followed by reduction of the resulting product with NaBH4 in methanol affords 1-(4-benzyloxyphenoxy)-2S-3-dihydroxypropane (V), which is monotosylated with tosyl chloride in pyridine giving the tosyl derivative (VI). The reaction of (VI) with isopropylamine (VII) in hot ethanol affords (S)-3-isopropylamino-1-(4-benzyloxyphenoxy)-2-propanol (VIII), which is finally debenzylated by reduction with H2 over Pd/C in ethanol.