Asymmetric synthesis of 3-substituted furanoside compound

PURPOSE: To prepare newly the subject compound having antiviral activity, etc., by allowing a specific compound to react with propargyl alcohol, and then allowing to react by adding lithium aluminum hydride, etc. CONSTITUTION: The compound of formula IV (M is a 1-3C alkyl) is obtained by allowing a compound of formula I (X is Cl or Br) to react with propargyl alcohol to obtain 5-hexene-2-yn-1-ol, then reducing the compound with lithium aluminum hydride to obtain an allyl alcohol, i.e., trans-2,5-hexadien-1-ol, asymmetrically epoxidizing the allyl alcohol in the presence of diisopropyl D-(-)-tartrate to form 2R,3R-epoxy-5-hexen-1-ol, allowing the compound to react with a reagent having nucleophilic substitutent to obtain a compound of formula II [A is a nucleophilic substituent such as a halogen, formula III (R is H, a 1-4C alkyl or phenyl), -OR, -N 3 ], ozonizing the compound of formula II, and catalytically hydrogenating the resulting compound with hydrogen on palladium-carbon catalyst. For example, methyl 3-fluoro-2,3-dideoxy-α,β-D-erythro-pentofuranoside. COPYRIGHT: (C)1993,JPO