The Development of a Generally Synthetic Method of D-and L-Deoxyfuranose

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1.The reaction of the allyl anion derived from 1-methoxy-3-(phenylthio)-1-propene with benzyl(R)-glycidyl ether was provided(E,S)-6-benzyloxy-5-hydroxy-2-hexenal, which was then transformed into(E,S)-6-benzyloxy-5-tert-butyldimethylsiloxy-2-hexen-1-ol in two steps : (a)tert-BuMe_2SiCl ; (b)NaBH_4 Sharpless-Katsuki asymmetric epoxidation with D-diethyl tartrate followed by treatment with C_6H_5CH_2OH afforded(2R,3S,5S)-3,6-bis(benzyloxy)-5-tert-butyldimethylsiloxy-1,2-hexanediol. This compound was treated successively with 2-methoxypropene, tetrabutylammonium fluoride, H_2-Pd/C,NalO_4, and diluted HCl to give D-2-deoxyribofuranose.2.(2S,3R,5S)-3,6-bis(benzyloxy)-5-tert-butyldimethylsiloxy-1,2-hexanediol was obtained using L-diethyl tartrate instead of D-diethyl tartrate in the method of 1.The vic-diol was treated successively Bu_4NF,NalO_4, and H_2-Pd/C to afford D-3-deoxyribofuranose.3.D-3-Azido-2,3-dideoxyribofuronose was prepared using NaN_3 instead of C_6H_5CH_2OH in the method of 1.4.D-2,3-Dideoxyribofuranose was obtained using LiAlH_4 instead of C_6H_5CH_2OH,on the other hand, L-2,3-dideoxyribofuranosewas produced by using(S)-glycidyl ether, L-diethyl tartrate, and LiAlH_4 according to the method of 1, respectively.5.According to the method of 1, D-2-deoxy-4-methylribofuranose and D-2-deoxy-3-methylribofuranose were obtained using of 1-methoxy-2-methyl-3-(phenylthio)-1-propene and 1-methoxy-3-(phenylthio)-1-butene, respectively.