Sugars Containing a Carbon-phosphorus Bond. II. Syntheses of Phosphinyl Sugars by the Michaelis-Arbuzov Reaction of Halogenated Sugars

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3,5-O-Benzylidene-6-deoxy-6-diethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose was prepared in an 80% yield by heating a solution of 3,5-O-benzylidene-6-deoxy-6-iodo-1,2-O-isopropylidene-α-D-glucofuranose (1) in an excess of triethyl phosphite (5). Similarly, 6-deoxy-6-diethoxyphosphinyl-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose was prepared in a 95% yield from 6-deoxy-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose (2), and (5); 5-deoxy-5-ethoxyphenylphosphinyl-1,2-O-isopropylidene-3-O-methyl-α-D-xylofuranose was prepared in a 90% yield from 5-bromo-5-deoxy-l,2-O-isopropylidenne-3-O-methyl-α-D-xylofuranose and diethyl phenylphosphonite; 3,5-O-benzylidene-6-deoxy- 1,2-O-isopropylidene-6- (N,N′-tetraethyldiaminophosphinyl)-α-D-glucofuranose was prepared in a 44% yield from 1 and ethyl N,N′-tetraethylphosphorodiamidite (7); 6-deoxy-1,2; 3,4-di-O-isopropylidene-6-(N,N′-tetraethyldiaminophosphinyl)-α-D-galactose was prepared in a 70% yield from 2 and 7.
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