Addition reactions of glycosid-4-uloses and related compounds with some phosphorus compounds

Abstract

Methyl 6-deoxy-2,3- O-isopropylidene-α- l- lyxo-hexopyranosid-4-ulose ( 2) was treated with methyl phenylphosphinate in the presence of triethylamine, to give mainly methyl 6-deoxy-2,3- O-isopropylidene-4- C-[(methoxy)phenylphosphinyl]-α- l-talopyranoside. Treatment of compound 2 with dimethyl and diethyl phosphonate under the same reaction conditions also afforded adducts having the l- talo configuration. The reaction of (6- S)-tetrahydro-6-methoxypyran-3-one with dimethyl phosphonate and methyl phenylphosphinate, respectively, gave the corresponding adducts in good yields. The reaction of methyl 2,3- O-isopropylidene-α,β- l- erythro-pentopyranosid-4-ulose and 2,3,5-tri- O-benzyl- aldehydo- l- threo-pentos-4-ulose 1-(dimethyl acetal) with methyl and phenyl phenylphosphinate also gave the corresponding adducts. These results suggest that the substituents on the sugar skeleton play an important role in the addition of phosphorus compounds.