Yuki Gosei Kogyo Co., Ltd.

Japan Tobacco Inc.

Kuraray Co., Ltd.

Mitsui Petrochemical Industries, Ltd.

Japan Tabacco Inc.

Japan Tobacco Co.

Kazuo Itoh

Hajime Matsushita

Takashi Ebata

Yoshitake Naoi

Hiroshi Kawakami

Koshi Koseki

Junko Tanaka

Junji Ohki

Nobuhiro Mizutani

Katsuya Matsumoto

Sadao Wakumoto

Shigeki Higuchi

Hiromi Kaibara

Hajima Yoshikoshi

Atsufumi Manabe

Tokuji Hasegawa

Toshie Koike

Method for preparing 2'-3'-dideoxy-.beta.-nucleosides using

The instant invention is drawn to a method for manufacturing 2',3'-dideoxy-2',3'-didehydronucleoside compounds by reacting a ribonucleoside derivative wherein the hydroxyl in the 5'-position of the furanose ring of said ribonucleoside is protected by a silyl protective group, with an acid anhydride such as acetic anhydride in the presence of a catalyst such as hydrous zirconium oxide, and then subjecting the reaction product to decarboxylation. The decarboxylation can be effected by heating the reaction product. This method can be performed in a single step, and requires no reagents which are expensive or chemicals which should be handled with care. Hence, it serves to manufacture 2',3'-dideoxy-2',3'-didehydronucleosides easily at low cost.

Method of manufacturing 2',3'-dideoxy-2',3'-didehydronucleosides

2'-deoxy-.beta.-adenosine can be industrially and easily obtained without using expensive or dangerous materials by the process of the present invention, which comprises the steps of: preparing a salt of adenine from adenine, allowing to condense the salt with a derivative of pentofuranose to isolate a derivative of adenine, and then eliminating the protecting groups.

Process for preparing 2'-deoxy-.beta.-adenosine

According to the present invention, a dental adhesive comprising glyceryl mono(meth)acrylate and a polymerizable monomer having at least one olefinic double bond and capable of copolymerizing with said glyceryl mono(meth)acrylate is provided.

Dental adhesives

This invention provides a process for producing 3'-deoxy-'-fluorothymidine, which comprises allowing 3'-deoxy-'-fluoro-5'-mesylthymidine (the stating material) to react with an acetylating agent, selected from the group consisting of alkali metal salts of acetic acid, amine salts of acetic acid and ammonium acetate, in an aprotic, ploar solvent to form the 5'-acetyl derivative, and ammonium acetate, in an aprotic, polar solvent to form the 5'-acetyl derivative, and eliminating the 5'-acetyl group from this intermediate, thereby giving the objective 3'-deoxy-'-fluorothymidine. According to the process of this invention described above, the 5'-mesyl derivative can be efficiently acetylated, and 3'-deoxy-'-fluorotymidine can be obtained in a high yield.

Process for producing 3'-deoxy-3-'-fluorothymidine

(S)-4-hydroxymethyl-.gamma.-lactone is prepared by oxidizing dihydrolevoglucosenone with a peracid in an organic solvent. (S)-4-hydroxymethyl-.gamma.-lactone is prepared from levoglucosenone. First, levoglucosenone is catalytic hydrogenated, thereby dihydrolevoglucosenone is obtained. Next, dihydrolevoglucosenone thus obtained is oxidized with a peracid in an organic solvent, thereby (S)-4-hydroxymethyl-.gamma.-lactone is obtained. In this manner, (S)-4-hydroxymethyl-.gamma.-lactone can be obtained with high optical purity.

Method of producing (S)-4-hydroxymethyl-.gamma.-lactone

The present invention is a process for preparing 2'-deoxy-5-trifluoromethyl-.beta.uridine characterized in that a 5-trifluoromethyl-2,4-bis(triorganosilyloxy)pyrimidine and a 1-halogeno-2-deoxy-.alpha.-D-erythro-pentofuranose derivative are subjected to condensation reaction in chloroform to give a 1-(2-deoxy-.beta.-D-erythro-pentofuranoxyl)-5-trifluoromethyluracil derivative which is then subjected to the deprotection reaction to give 2'-deoxy-5-trifluoromethyl-.beta.-uridine.

Process for preparing 2'-deoxy-5-trifluoromethyl-beta-uridine

A method of preparing (S)-.gamma.-hydroxymethyl-.alpha.,.beta.-butenolide includes the step of oxidizing a levoglucosenone with a peracid in an organic solvent. Peracetic acid, metha-chloroperbenzoic acid or magnesium monoperoxyphthalate hexahydrate can be used as the peracid. According to this method, an (S)-.gamma.-hydroxymethyl-.alpha.,.beta.-butenolide having high optical purity can be easily prepared from a levoglucosenone as a starting material at a high yield.

Method of preparing (S)-.gamma.-hydroxymethyl-.alpha., .beta.-butenolide

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Tokyo, Japan

Kazuo Itoh