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late Gen-ichi Tsuchihashi

Bio: late Gen-ichi Tsuchihashi is an academic researcher from Keio University. The author has contributed to research in topics: Desosamine & Aliphatic compound. The author has an hindex of 3, co-authored 3 publications receiving 352 citations.

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Journal ArticleDOI
TL;DR: The combination of Cp 2 MCl 2 -AgClO 4, (M=Zr, Hf) is effective for the activation of glycosyl fluorides, which enables the highly β-selective glycoside formation of D-mycinose by performing the reaction in benzene.

194 citations

Journal ArticleDOI
TL;DR: In this article, a new activation system for glycosyi fluorides, Cp2 HfCl2-AgCIO4, enables highly efficient glycosidation of 1-fluoro-D-desosamine derivative.

119 citations

Journal ArticleDOI
TL;DR: In this article, the first total synthesis of mycinamicin IV via mycinamidein VII was described, and a new glycosidation reaction using Cp 2 MCl 2 -AgClO 4 (M=Zr, Hf) was effectively applied to the selective introduction of β-D-mycinosyI and βD-desosaminyl linkages.

50 citations


Cited by
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Journal ArticleDOI
TL;DR: Organic fluorine compounds have received a great deal of interest and attention from the scientists involved in diverse fields of science and technology and not only C-F bond formation but also selective C-f bond activation have become current subjects of active investigation from the viewpoint of effective synthesis of fluoroorganic compounds.
Abstract: Fluorine has received great attention in all fields of science. “Small atom with a big ego” was the title of the Symposium at the ACS meeting in San Francisco in 2000, where a number of the current scientific and industrial aspects of fluorine chemistry made possible by the small size and high electronegativity of the atom were discussed. This small atom has provided mankind with significant benefits in special products such as poly(tetrafluroethylene) (PTFE), freon, fluoro-liquid crystals, optical fiber, pharmaceutical and agrochemical compounds, and so on, all of which have their own unique properties that are otherwise difficult to obtain.1 For instance, at present, up to 30% of agrochemicals and 10% of pharmaceuticals currently used contain fluorine atoms. Therefore, organic fluorine compounds have received a great deal of interest and attention from the scientists involved in diverse fields of science and technology. Now, not only C-F bond formation but also selective C-F bond activation have become current subjects of active investigation from the viewpoint of effective synthesis of fluoroorganic compounds. The former is highlighted by designing a sophisticated fluorinating reagent for regioand stereocontrolled fluorination and developing versatile multifunctional and easily prepared building blocks. C-F bond formation has been treated extensively in several reviews2 and books.3 The latter is a subject that has been less explored but would be promising for selective defluorination of aliphatic fluorides, cross-coupling with aryl fluorides, and * To whom correspondence should be addressed. Phone: 81-78-803-5799. Fax: 81-78-803-5799. E-mail: amii@kobe-u.ac.jp and uneyamak@cc.okayamau.ac.jp. † Kobe University. ‡ Okayama University. Chem. Rev. 2009, 109, 2119–2183 2119

1,132 citations

Journal ArticleDOI
TL;DR: The field of carbohydrate chemistry has occupied the minds and hearts of many scientists for over a hundred years and, as we enter the twenty-first century, it continues to be both vigorous and challenging.
Abstract: The field of carbohydrate chemistry has occupied the minds and hearts of many scientists for over a hundred years and, as we enter the twenty-first century, it continues to be both vigorous and challenging. Among the most exciting aspects of organic chemistry in the last few decades has been the interplay between the specialized subdisciplines of carbohydrate chemistry and total synthesis, each enabling and advancing the other in new directions and towards greater heights. In this review article we highlight our own adventures at the interface of these disciplines, which were driven for the most part by objectives in chemical synthesis and chemical biology. Specifically, we describe our interests and efforts to utilize carbohydrates as starting materials for total synthesis, to invent and develop new synthetic technologies for carbohydrate synthesis, to construct complex oligosaccharides in solution or on solid support, and to utilize carbohydrate templates as scaffolds for peptide mimetics and for molecular diversity construction. Finally, applications of the developed synthetic strategies and enabling technologies towards the solution of biologically significant problems are discussed.

324 citations