Abstract: It is the problems to provide an effective production method for optically active N-aryl-&bgr;-amino acid compounds, which at the same time is suitable for industrial production. By the reaction of optically active sulfonylated &bgr;-hydroxycarboxylic acid compounds, which are easily derived from &bgr;-keto carboxylic acid compounds, with aromatic amines, optically active N-aryl-&bgr;-amino acid compounds are obtained.

Abstract: A production method for conveniently producing a 5′-acyloxynucleoside compound shown by the formula [A] in a good yield while suppressing formation of by-products, including subjecting a 2′,3′,5′-triacyloxynucleoside compound represented by the formula [I] to selective deacylation in an alcohol represented by the formula [II] using a base selected from the group consisting of alkali metal hydroxide, alkali metal alkoxide and alkali metal carbonate: 1

Abstract: Herein are disclosed a process for increasing in purity, or purifying, an N-protected-&bgr;-aminoalcohol which process comprises (i) adding water to a polar organic solvent in which an N-protected-&bgr;-aminoalcohol such as a (2R,3S)-or (2S,3R)-3-tert-butoxycarbonylamino-1-halo-2-hydroxy-4-phenylbutane or the like, or (ii) crystallizing such an N-protected-&bgr;-aminoalcohol from a diol or a diol-based mixed solvent, and a process for producing the corresponding N-protected-&bgr;-aminoepoxide which process comprises treating, with a base, the thus purity-enhanced N-protected-&bgr;-aminoalcohol. Such N-protected-&bgr;-aminoalcohols and N-protected-&bgr;-aminoepoxides are both useful as synthetic intermediates for medicine compounds, such as, e.g., HIV protease inhibitor and the like.

Abstract: A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

Abstract: The present invention provides a method for efficiently producing &bgr;-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzyl-&bgr;-D-ribofuranose-2,3,5-triacetate or an optical isomer thereof by allowing &bgr;-D-ribofuranose-1,2,3,5-tetraacetate or an optical isomer thereof to react with a benzyl alcohol in the presence of acid catalysts and a step of hydrolyzing the resulting 1-O-benzyl-&bgr;-D-ribofuranose-2,3,5-triacetate in the presence of a base to produce 1-O-benzyl-&bgr;-D-ribofuranose or an optical isomer thereof.

Abstract: The invention relates to a method for industrially producing highly pure (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoepoxide (crystal) or (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoalcohol.

Abstract: The present invention provides a production method including adding water to a solution of (2R,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane ((2R,3S)-epoxide compound) or (2S,3R)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane ((2S,3R)-epoxide compound) in a polar solvent to allow crystallization, whereby to produce crystals of the (2R,3S)-epoxide compound or the (2S,3R)-epoxide compound conveniently in a high yield by an industrial production method without requiring an extremely low temperature.

Abstract: An N-9-position alkylated form is selectively precipitated by subjecting a mixture containing the N-9-position alkylated form and an N-7-position alkylated form of 2-amino-6-halopurine to a crystallization step using a mixed solvent of an organic solvent and water. Then, this N-9-position alkylated form is reduced to give famciclovir. By this method of the present invention, famciclovir known as an antiviral agent, and an intermediate compound therefor can be efficiently produced.

Abstract: The present invention provides a method for industrially producing an optically active lysine derivative useful as a pharmaceutical intermediate. More particularly, the present invention provides a production method including protecting an amino group or an amino group and carboxyl group of optically active 2-amino-6-methyl-6-nitroheptanoic acid with a protecting group, reducing a nitro group to synthesize a 6,6-dimethyl lysine derivative and reacting the 6,6-dimethyl lysine derivative with an acetic acid derivative.

Abstract: A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

Abstract: An amino group of an &agr;-amino acid ester is protected as an imine, and it is then reacted with a halomethyllithium to obtain an N-protected-&agr;-aminohalomethylketone. Further, this N-protected-&agr;-aminohalomethylketone is treated with an acid to obtain an &agr;-aminohalomethylketone. This process is suited for industrial production, and can produce an &agr;-aminohalomethylketone and its related compounds economically and efficiently.

Abstract: The present invention provides a method for industrially producing an optically active lysine derivative useful as a pharmaceutical intermediate. More particularly, the present invention provides a production method including protecting an amino group or an amino group and carboxyl group of optically active 2-amino-6-methyl-6-nitroheptanoic acid with a protecting group, reducing a nitro group to synthesize a 6,6-dimethyl lysine derivative and reacting the 6,6-dimethyl lysine derivative with an acetic acid derivative.

Abstract: There can be provided an excellent industrial process for producing compounds having sugar-moiety hydroxyl groups or halogen atoms reduced in nucleic acids or in derivatives thereof by allowing O-thiocarbonyl derivatives of sugar-moiety hydroxyl groups or allowing halogenated derivatives in the sugar-moiety, in the nucleic acids or in derivatives thereof to react with any one of hypophosphorous acids (including salts thereof) and phosphites (esters) which are inexpensive, non-toxic and safely usable as radical reducing agents in industrial scale, in the presence of a radical reaction initiator.

Abstract: Novel intermediates of nucleoside derivatives, of which the 6-position of the nucleic acid base moiety is substituted with a halogen atom, are produced. Using those novel intermediates, even substrates, of which the 3′-position of the saccharide moiety is deoxylated, can be substituted at the 2′-position at an extremely high yield. Specifically, by subjecting a 3′-deoxy derivative of inosine to 6-halogenation to give a 6-halide of the derivative, and then subjecting it to 2′-deoxylation/substitution with a fluorine atom or the like, followed by further subjecting it to substitution with an amino group, a hydroxyl group or any other intended substituent at the 6-positioned halogen atom, nucleoside derivatives are produced at a high yield.

Abstract: A process for producing &agr;-amino-dihalogenated methyl ketone derivatives by reacting an N-protected &agr;-amino acid ester with a dihalomethyl lithium is provided. This process is suitable for the production on an industrial scale and by this process, &agr;-amino-dihalogenated methyl ketone derivatives and &bgr;-amino-&agr;-hydroxycarboxylic acid derivatives can be obtained efficiently and economically advantageously.

Abstract: There can be provided an excellent industrial process for producing compounds having sugar-moiety hydroxyl groups or halogen atoms reduced in nucleic acids or in derivatives thereof by allowing O-thiocarbonyl derivatives of sugar-moiety hydroxyl groups or allowing halogenated derivatives in the sugar-moiety, in the nucleic acids or in derivatives thereof to react with any one of hypophosphorous acids (including salts thereof) and phosphites (esters) which are inexpensive, non-toxic and safely usable as radical reducing agents in industrial scale, in the presence of a radical reaction initiator. The process of the present invention is an industrially useful and highly safe process for reducing sugar-moiety hydroxyl groups and halogen atoms in nucleic acids or derivatives thereof (including nucleic acid-related compounds) at low costs.

Abstract: The present invention provides a method for industrially producing an optically active lysine derivative useful as a pharmaceutical intermediate. More particularly, the present invention provides a production method including protecting an amino group or an amino group and carboxyl group of optically active 2-amino-6-methyl-6-nitroheptanoic acid with a protecting group, reducing a nitro group to synthesize a 6,6-dimethyl lysine derivative and reacting the 6,6-dimethyl lysine derivative with an acetic acid derivative.

Abstract: A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

Abstract: A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

Abstract: An amino group of an &agr;-amino acid ester is protected as an imine, and it is then reacted with a halomethyllithium to obtain an N-protected-&agr;-aminohalomethylketone. Further, this N-protected-&agr;-aminohalomethylketone is treated with an acid to obtain an &agr;-aminohalomethylketone. This process is suited for industrial production, and can produce an &agr;-aminohalomethylketone and its related compounds economically and efficiently.