11 0 0 0 OA 無臭有機硫黄反応剤の開発と応用
- 著者
- 西出 喜代治 野出 學
- 出版者
- The Society of Synthetic Organic Chemistry, Japan
- 雑誌
- 有機合成化学協会誌 (ISSN:00379980)
- 巻号頁・発行日
- vol.62, no.9, pp.895-910, 2004-09-01 (Released:2010-01-22)
- 参考文献数
- 39
- 被引用文献数
- 15 15
Development of odorless thiols [1-dodecanethiol (Dod-SH), 4-trimethylsilylphenylmethanethiol (TMSBM), 4-trimethylsilylbenzenethiol (TMSBT), and 6-morpholinohexanethiol (MHT)] and odorless sulfides [dodecyl methyl sulfide (Dod-S-Me), methyl 6-morpholinohexyl sulfide (MMS)] and their sulfoxides [dodecyl methyl sulfoxide (Dod-S (O) -Me), methyl 6-morpholinohexyl sulfoxide (MMSO)] as odorless substitutes for the foul-smelling ethanethiol, benzyl mercaptan, benzenethiol, and dimethyl sulfide (DMS) is described. They are conveniently applied for dealkylation, thiol exchange reaction, reductive ozonolysis, Corey-Kim oxidation, Swern oxidation, hydroboration, and reduction. The products of these reactions utilizing morpholine based thiol MHT, sulfide MMS and its sulfoxide MMSO can be easily purified by only acid-base extraction without involving chromatography, thereby eliminating unpleasant odors, saving time and protecting the environment. In view of current environmental and economic factors, the utility of these simple reagents could be enormously beneficial.
1 0 0 0 A Synthesis of New 3-Dialkoxyphosphinylmethyl and 3-Dihydroxy-phosphinylmethyl Cephalosporins
- 著者
- 西出 喜代治 山村 真理子 小堀 武夫 常本 大英 近藤 聖 佐藤 清
- 出版者
- 公益社団法人日本薬学会
- 雑誌
- Chemical & pharmaceutical bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.36, no.7, pp.2354-2361, 1988-07-25
The syntheses and the antibacterial activities of new 3-dimethoxyphosphinylmethyl and 3-dihydroxyphosphinylmethyl cephalosporins I-(Z), II-(Z), III-(Z) and III-(E), possessing the chloromethylene or methoxyimino substituent at the α-position to the 7-(2-aminothiazol-4-yl)acetamido or 7-(thiazol-4-yl)acetamido moiety of the cephem nucleus, are described. The key steps of these syntheses were the Michaelis-Arbusov reaction of the 3-halomethylcephem 1 with trimethyl phosphite and the dealkylation reactions of both the dimethoxyphosphinyl group and the p-methoxybenzyl ester of 7a, b-(Z) by treatment with bromotrimethylsilane to afford 9a, b-(Z).