著者

平井 功一 丸山 洋

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.57, no.5, pp.382-386, 1999-05-01 (Released:2009-11-16)

参考文献数

9

被引用文献数

1 1

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Several problems encountered during the kg scale production of such an unstable carbapenem antibiotic “Panipenem” (CS-533) was overcome by scrutinizing the reaction conditions and the factors influencing the reactions. Each item was reviewed from the nostalgic standpoint of a basic organic chemist, and the hard work of isolation technology is described at the same time.

著者

高松 聡 丸山 徳見 井澤 邦輔

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.63, no.9, pp.864-878, 2005-09-01 (Released:2009-11-13)

参考文献数

39

被引用文献数

2 3

---

Lodenosine, [9- (2, 3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl) adenine, FddA, 1] is an acid-stable purine nucleoside analog with activity against human immunodeficiency virus (HIV). There are two possible approaches to 1 - the glycosylation of a nucleoside base with a fluorinated sugar or direct nucleoside fluorination. However, both methods have drawbacks in terms of the number of steps, the use of toxic agents and low overall yields. In this review article, we describe two industrial synthetic approaches to 1 via 6-chloropurine riboside and 6-chloropurine 3'-deoxyribo-side, the latter being derived from inosine, a readily available starting material produced by fer-mentation. Several deoxygenation and fluorination methods are compared considering reaction yields, cost, safety and environmental concerns.

著者

飯沼 勝春 村井 安

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.57, no.5, pp.368-373, 1999-05-01 (Released:2009-11-16)

参考文献数

7

被引用文献数

2 2

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Arbekacin, aminoglycoside antibiotic, was synthesized in 1973 by Kondo et al starting from Dibekacin by the acylation of 1-amino group with (S) -4-amino-2-hydroxybutyric acid (AHB), and approved as a chemotherapeutic agent in 1990 limiting to MRSA infection. In the development of industrial large scale synthesis, the main theme was selective protection of four amino groups except 1-amino group. We focused our effort to set up large scale synthetic method by taking advantage of zinc-chelation reaction. By the optimization of reaction conditions and minimization of isolation procedures, final production method was completed. We herein report the development course of high yield and low cost production method by the selective protection of amino group.

著者

西脇 正憲

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.61, no.5, pp.464-471, 2003-05-01 (Released:2009-11-13)

参考文献数

12

被引用文献数

3 4

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Recently, green chemistry (GC) plays an important role for manufacturing active pharmaceutical ingredients (APIs) at pharmaceutical companies. For example, large amount of aluminum waste was originally involved and dichloromethane used as a solvent in the process of a new anticholinergic agent, Vamicamide (FK 176), useful for the treatment of urinary incontinence. Non-selective and tedious procedures for alkylation of quinazoline nucleous were used on a laboratory scale in the process of a novel aldose reductase inhibitor, Zenarestat (FK 366) developed for the remedy of diabetic complications. These problems must be excluded before realizing a truly efficient process on a large scale. New process involved much less amount of waste in the case of Vamicamide, and utilized regioselective alkylation reaction for Zenarestat. As a result, E-factor and reaction mass efficiency (RME) were dramatically improved. Herein, we report our efforts leading to an efficient, practical and environmentally friendly process amenable to a large scale synthesis.

著者

橋本 俊一 本田 雄 柳谷 由己 中島 誠 池上 四郎

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.53, no.7, pp.620-632, 1995-07-01 (Released:2009-11-16)

参考文献数

38

被引用文献数

4 6

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The rational design and development of stereocontrolled glycosidation reactions has been the subject of intensive investigations. Our interest in this context has been centered on the design of the leaving groups of glycosyl donors coupled with their activation without resorting to precious, explosive, or toxic heavy-metal salts as promoters. In an effort to capitalize on the phosphorus-containing leaving groups, we have recently devised new glycosyl donors incorporating diphenyl phosphate, diphenylphosphinimidate, N, N, N', N'-tetramethylphosphoroamidate, phosphorodiamidimidothioate, or diethyl phosphite as leaving groups, the glycosidations of which constitute mild and efficient methods for the highly stereocontrolled construction of 1, 2-trans-β-and 1, 2-cis-α-glycosidic linkages. In this paper, several notable features of the present glyosidation methods coupled with the mechanistic aspects are described.

著者

池上 四郎 柴崎 正勝

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.38, no.11, pp.1037-1052, 1980-11-01 (Released:2010-04-23)

参考文献数

67

被引用文献数

5 6

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This review, including two parts, deals with recent progress in the prostaglandin field. The first part is concerned with the synthetic studies of endoperoxides, thromboxanes, prostacyclins and leukotrienes. The second describes briefly the biological properties of various stable synthetic analogs.

著者

浦口 大輔 大井 貴史

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.76, no.11, pp.1144-1153, 2018-11-01 (Released:2018-11-09)

参考文献数

97

被引用文献数

8

---

The ammonium betaine was developed as an intramolecular ion-pair catalyst for realizing cooperative catalysis of a cation and anion; i.e. ion-pair catalysis. Combination of the stereocontrolling ability of the chiral ammonium ion and functions of the pairing aryloxylate ion enabled bifunctional organic base catalysis and ionic nucleophilic catalysis, which facilitate a variety of organic transformations with rigorous stereochemical control. In addition, employing a single-electron-accepting cation as a partner of the basic aryloxylate led to the development of a chemical redox catalyst with the capability of proton-coupled electron transfer (PCET). This research demonstrates a power of the ion-pair catalysis in selective organic synthesis and is therefore likely to stimulate further study in this field.

著者

増尾 栄太郎

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.18, no.10, pp.718-724, 1960-10-01 (Released:2010-10-20)

参考文献数

27

被引用文献数

1

著者

細見 彰 櫻井 英樹

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.43, no.5, pp.406-418, 1985-05-01 (Released:2009-11-13)

参考文献数

117

被引用文献数

15 18

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Allylsilanes can provide synthetic strategies which are not achieved with other allylic metal reagents such as the Grignard, lithium and transition metal reagents. In this review article, the characteristics in the reactions of allylsilanes, especially not only enhanced reactivities towards various electrophiles due to σ-π conjugation but also regio-, stereo-, and chemoselectivities, are surveyed. Moreover, a variety of allylsilanes that have been synthesized and utilized as versatile synthetic equivalents are summarized.

著者

林 喜世茂

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.32, no.6, pp.471-479, 1974-06-01 (Released:2009-11-13)

参考文献数

7

著者

津吹 政可

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.51, no.5, pp.399-411, 1993-05-01 (Released:2010-01-28)

参考文献数

59

被引用文献数

10 13

---

Furans have been recognized as useful intermediates in organic synthesis. Among the synthetic utilities of furans, 1, 4-dicarbonyl equivalence is one of the characteristic features. This article describes the methodology for the synthesis of natural products, such as physiologically active steroids and lactonic antibiotics, employing the 1, 4-dicarbonyl equivalents derived from furan derivatives. The synthetic strategy is based on oxidative conversion of chiral furfuryl alcohols into the pyranones followed by their functionalization with appropriate nucleophiles and electrophiles to provide the modified pyrans possessing desired stereochemistries. These intermediates have been transformed into withanolide and brassinolide side chains, styryl lactones such as goniothalamin and goniodiol, malyngolide, and canadensolide. Chiral furfuryl alcohols have been prepared as follows. 1) Diastereoselective addition of 2-lithiofurans to chiral carbonyl compounds. 2) Kinetic resolution of secondary furfuryl alcohols using Sharpless reagent.

著者

伊藤 雄三

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.49, no.5, pp.432-436, 1991-05-01 (Released:2009-11-16)

参考文献数

17

被引用文献数

2 4

---

In order to design organic nonlinear optical materials, several of theoretical calculations are necessary. Within the oriented gas model approximation, nonlinear susceptibilities of organic crystals can be calculated from hyperpolarizabilities of the molecule and the crystal structure. Molecular hyperpolarizabilities can be calculated very precisely by a molecular orbital method. Theoretical calculations of hyperpolarizabilities of polymers, which are important as third-order nonlinear materials, were done considering their exciton states although there remained several problems to be solved. The intermolecular interaction effects on hyperpolarizabilities were analysed by super molecule CPHF calculations of ab initio MO method.

著者

多羅間 公雄

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.16, no.9, pp.433-446, 1958-09-01 (Released:2010-10-20)

参考文献数

96

被引用文献数

5 4

著者

川上 浩 惠畑 隆 松下 肇

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.50, no.6, pp.535-544, 1992-06-01 (Released:2010-01-28)

参考文献数

62

被引用文献数

1 2

---

Many nucleoside analogues, which lack 2'-substituents, have been known to be a useful compound as anticancer and anti-virus agents. On the other hand, synthesis of these derivatives utilizing the condensation reactions between sugars and nucleic bases have a difficulty in the stereoselectivity of these reactions. In this paper, our investigation on the condensation reactions with some 2-deoxysugars are discussed in the point of stereoselectivity. Transformations to 2', 3'-dideoxynucleosides and 2', 3'-didehydro-2', 3'-dideoxynucleosides are also described.

著者

村上 正志 西田 進也

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.41, no.1, pp.22-37, 1983-01-01 (Released:2010-04-23)

参考文献数

137

被引用文献数

11 12

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Chemical characteristics of cyclopropyl derivatives are classified and organic syntheses with practical utilization of these characteristics are reviewed. The classification involves : (1) additions of X-Y to a strained cyclopropyl sigma bond with ring cleavage; (2) additions of a nucleophile to activated cyclopropyl derivatives; (3) isomerizations of cyclopropyl cations, anions, and radicals to allylic species; (4) isomerizations of cyclopropylmethyl cations, anions, and radicals to either cyclobutyl or 3-butenyl species; (5) allenes from cyclopropylidenes and cyclopentadienes from 2-vinylcyclopropylidenes; (6) rearrangement of cyclopropylcarbenes to cyclobutenes; (7) reactions involving homolytic cleavage of a cyclopropane sigma bond; (8) vinylcyclopropane-cyclopentene rearrangement; (9) cis-1, 2-divinylcyclopropane-cyclohepta-1, 4-diene rearrangement and homo-1, 5-hydrogen migration; (10) homolyses of cyclopropene yielding vinylcarbenes ; (11) cycloadditions of some specifically activated olefins to cyclopropane derivatives; and (12) reactions of cyclopropene derivatives followed by ring cleavage of the resultant three-membered ring compounds.

著者

碇屋 隆雄 ジェソップ フィリップ G. 野依 良治

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.53, no.5, pp.358-369, 1995-05-01 (Released:2010-04-23)

参考文献数

48

被引用文献数

4 5

---

Most homogeneous catalysts have higher selectivity but lower rates than heterogeneous catalysts in gas-phase reactions. An ideal catalyst would have the best of both worlds, high selectivity and high rates which may be possible with homogeneous catalysts in supercritical fluids rather than liquid solvents. These fluids are compressed gases heated past their critical point. Preliminary results have confirmed that increased rates and selectivities can be obtained because of several unusual properties of supercritical fluids : high solubility of reactant gases, rapid diffusion between phases, and possibly weaker solvation of the catalyst. This review will describe research on organic reactions and homogeneous catalysis in supercritical fluids, with emphasis on supercritical carbon dioxide and water as reaction media.

著者

大津 隆行

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.33, no.8, pp.634-640, 1975-08-01 (Released:2009-11-13)

参考文献数

43

著者

村山 徹郎

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.57, no.6, pp.541-551, 1999-06-01 (Released:2009-11-16)

参考文献数

59

被引用文献数

2 6

---

Electrophotography is one of the most prevalent copier and printer technologies. Photoreceptors play a major role in the electrophotographic process. Nowadays, organic photoconductive materials have been most widely used for photoreceptors. Azo and Phthalocyanine pigments are major charge carrier generation materials (CGMs). Hydrazones and arylamines are used as charge carrier transport materials (CTMs). Some models for carrier generation and transport mechanisms have been proposed, Based on these models, molecular structural effects of CGMs and CTMs have been investigated and some new compounds showing good performances have been synthesized.

著者

藤沢 有 佐藤 俊夫 伊藤 敏幸

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.44, no.6, pp.519-531, 1986-06-01 (Released:2009-11-13)

参考文献数

83

被引用文献数

27 29

---

The baker's yeast mediated reduction of ketones with various kinds of functional groups provides a useful method for the synthesis of optically active secondary alcohols. Compared with the usual chemical methods using chiral metal hydride reagents, the advantages of the present method are the easier availability of the yeast, milder reaction conditions, i. e. at room temperature in water under air atmosphere, higher optical yield and chemoselectivity especially in the reduction of saturated ketones. Asymmetric reduction of carbon-carbon double bond and the carbon-carbon bond forming reaction of α, β-unsaturated carbonyl compounds are also accomplished by baker' s yeast. The products thus obtained are applied as chiral building blocks to the synthesis of various natural products.

著者

島村 忠男

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.45, no.12, pp.1209-1210, 1987-12-01 (Released:2009-11-13)

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シアヌル酸クロリドの主要製品は四種類あり, そのうち生産量の最も多いものはシアヌル酸トリクロリド (TICA), 次に多いのがシアヌル酸ナトリウムジクロリド (SDIC) である。そのあとにシヌアル酸ナトリウムジクロリド2水和物 (DICD) とシアヌル酸カリウムジクロリド (PDIC) が続く。TICAはIUPAC命名法で1, 3, 5-トリクロロ-1, 3, 5-トリアジン-2, 4, 6-トリオン, 慣用名はトリクロルイソシアヌル酸または三塩素化イソシアヌル酸である。