Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors

• Georg Schitter,
• Elisabeth Scheucher,
• Andreas J. Steiner,
• Arnold E. Stütz,
• Martin Thonhofer,
• Chris A. Tarling,
• Stephen G. Withers,
• Jacqueline Wicki,
• Katrin Fantur,
• Eduard Paschke,
• Don J. Mahuran,
• Brigitte A. Rigat,
• Michael Tropak and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2010, 6, No. 21, doi:10.3762/bjoc.6.21

• desired free amine 15 [25], the key building block for further modifications (Scheme 2). The chemoselective acylation of the free amine 15 was conducted with three different benzoic acid derivatives in order to investigate the influence of the potential basicity of an additional nitrogen at the aromatic

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• , Kessler and co-workers have reported the synthesis of cyclic oligomers containing glucopyranosyluronic acid by exploiting standard solid and solution phase coupling procedures [54]. These cyclic homo-oligomers of SAAs behave as host molecules that form inclusion complexes with p-nitrophenol and benzoic

• acid. Following the same objective, Xie’s group prepared orthogonally protected cyclic homo-oligomers with two to four SAA units that can be selectively or fully deprotected to afford macrocycles that can undergo further functionalisation (Figure 11) [55]. Conformational analysis by molecular modelling

N-alkyl-N-(phosphonoethyl) substituted (meth)acrylamides – new adhesive monomers for self-etching self-priming one part dental adhesive

• Joachim E. Klee and
• Uwe Lehmann

Beilstein J. Org. Chem. 2009, 5, No. 72, doi:10.3762/bjoc.5.72

• , trimethylbromosilane, butylamine, 3,6-dioxaoctane-1,8-diamine, camphorquinone and 4-(N,N-dimethylamino)benzoic acid ethyl ester, diethyl (hydroxymethyl)phosphonate, 2,2′-azobisisobutyronitrile (AIBN) and 2,6-di-tert-butyl-4-methylphenol were purchased from Sigma-Aldrich and phenylbis(2,4,6-trimethylbenzoyl)phosphine

• mol % camphorquinone and 0.35 mol % 4-(N,N-dimethylamino)benzoic acid ethyl ester. The hydrolytic stability was studied by detection of acrylic or methacrylic acid in HPLC using solutions of 1.5 mmol of 3c, 3d and 3e and solutions of 0.6 mmol 3g in 5 mL of a 1:1 mixture of distilled water and ethanol

• , 0.0083 g 4-(N,N-dimethylamino)benzoic acid ethyl ester and 0.0179 g bis bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide were dissolved in a solvent mixture composed of 0.5000 g ethanol and 0.5000 g water. The following procedure was applied prior to adhesion measurement: At first teeth were abraded by

Novel banana-discotic hybrid architectures

• Hari Krishna Bisoyi,
• H. T. Srinivasa and
• Sandeep Kumar

Beilstein J. Org. Chem. 2009, 5, No. 52, doi:10.3762/bjoc.5.52

• (hexyloxy)triphenylene-2-yloxy]dodecyloxy}benzoic acid (4): A mixture of compound 3 (2.3 g) dissolved in 1,4-dioxane (20 ml) and 5% Pd-C catalyst (0.4 g) was stirred in an atmosphere of hydrogen until the required quantity of hydrogen was absorbed. The resulting mixture was filtered in hot and the solvent

Gold film- catalysed benzannulation by Microwave- Assisted, Continuous Flow Organic Synthesis (MACOS)

• Gjergji Shore,
• Michael Tsimerman and
• Michael G. Organ

Beilstein J. Org. Chem. 2009, 5, No. 35, doi:10.3762/bjoc.5.35

• -benzoic acid (1.71 mmol, 250 mg) in 6 mL of dry THF was added over 10 min. When the addition of acid was complete, 3 drops of DMF were added to the mixture and bubbling was observed. After stirring for 30 min. at 0 °C, the solution was stirred an additional 30 min. at rt, and then cooled back to 0 °C

• -carbonyl)naphthalen-2-yl]-benzoic acid (4e). Following the general MACOS benzannulation protocol, 2-(2-(thiophen-3-yl)-ethynyl)-benzaldehyde (1d) and 3-ethynylbenzoic acid were reacted and 700 μL of the crude reaction mixture were collected. Purification by flash chromatography (10% methanol in

Silica- bound benzoyl chloride mediated the solid- phase synthesis of 4H-3,1-benzoxazin- 4-ones

• Kurosh Rad-Moghadam and
• Somayeh Rouhi

Beilstein J. Org. Chem. 2009, 5, No. 13, doi:10.3762/bjoc.5.13

• synthesis of SBBC through which first the surface of silica gel was converted to silica chloride by means of reaction with thionyl chloride [27][28]. The silica chloride was heated with 4-hydroxybenzoic acid to form the silica-bound benzoic acid (SBBA). The SBBA was washed with acetone to remove excess 4

Trifluoromethyl ethers – synthesis and properties of an unusual substituent

• Frédéric R. Leroux,
• Baptiste Manteau,
• Jean-Pierre Vors and
• Sergiy Pazenok

Beilstein J. Org. Chem. 2008, 4, No. 13, doi:10.3762/bjoc.4.13

• lithiation next to the OCF3 substituent is favoured, probably due to steric reasons. In fact, 1-trifluoromethoxy-4-(trifluoromethyl)benzene (Scheme 15) affords 2-trifluoromethoxy-5-(trifluoromethyl)benzoic acid after lithiation and carboxylation [75]. When the OCF3 substituent is in competition with fluorine

Electronic differentiation competes with transition state sensitivity in palladium- catalyzed allylic substitutions

• Dominik A. Lange and
• Bernd Goldfuss

Beilstein J. Org. Chem. 2007, 3, No. 36, doi:10.1186/1860-5397-3-36

• of substrate and catalyst structures. "Side arm guidance" of nucleophiles with multifunctional phosphinoferrocenes [14][15][16][17][18] or "chiral pockets" in C2-symmetric diphosphanes based on 2-(diphenyl-phosphino)benzoic acid amides [19][20][21][22] were applied especially successfully. Chiral P,N

EcoScale, a semi- quantitative tool to select an organic preparation based on economical and ecological parameters

• Koen Van Aken,
• Lucjan Strekowski and
• Luc Patiny

Beilstein J. Org. Chem. 2006, 2, No. 3, doi:10.1186/1860-5397-2-3

• benzoic acid [24] Synthesis of benzamide [25] Synthesis of benzamide using HMDS [26] The penalty points to calculate the EcoScale The penalty points for example 1 The penalty points for example 2 The penalty points for example 3 The penalty points for example 4