10,12-Tricosadiynoic acid

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 10,12-tricosadiynoic acid (10 gm, GFS Chemicals) was dissolved in a solution containing 10 ml methanol (HPLC grade) and 10 ml chloroform (HPLC grade). The solution was stirred at room temperature and 10 drops of neat sulfuric acid was added drop wise. The solution was warmed to 100° F. for 2 hour. The reaction mixture was purified using column chromatography. The product (MeTDA) was dried using a rotovap and the material stored in a chloroform solution. The solid form of MeTDA was very unstable to polymerization and therefore kept dissolved in organic solutions. Alcoholic solutions of MePDA and MeTDA: Solids MePDA or MeTDA were dissolved in reagent grade ethanol to a concentration of 150 mg/ml. An residual polymer was removed by filtration through Whatman No. 1 filter paper. The solutions was held at room temperature or slightly above (70-75° F.) to avoid crystallization or precipitation. The solution was warmed to 100° F. for 2 hour The reaction mixture was purified The product (MeTDA) was dried The solid form of MeTDA was very unstable to polymerization kept dissolved in organic solutions An residual polymer was removed by filtration through Whatman No 1 filter paper was held at room temperature or slightly above (70-75° F.) crystallization or precipitation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Alcoholic Monomer Solution of TDA/PDA: 10,12-Tricosadiynoic acid (TDA, 6 gm GFS Chemicals) and 10,12-pentacosadiynoic acid (PDA, 0.9 gm GFS Chemicals) were dissolved in 60 ml ethanol (Fisher). The solution was slightly warmed and stirred. The solution (TDA/PDA) was filtered (Whatman No. 1) to remove residual polymer. Dye colorant could be added to the alcoholic monomer solution as an indicator. Standard organic solvent based dyes were added at 2 drops per ml. The solution was slightly warmed The solution (TDA/PDA) was filtered (Whatman No. 1) to remove residual polymer Dye colorant could be added to the alcoholic monomer solution as an indicator were added at 2 drops per ml

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Alcoholic Monomer Solution of TDA/PDA: 10,12-Tricosadiynoic acid (TDA, 6 gm GFS Chemicals) and 10,12-pentacosadiynoic acid (PDA, 0.9 gm GFS Chemicals) were dissolved in 60 ml ethanol (Fisher). The solution was slightly warmed and stirred. The solution (TDA/PDA) was filtered (Whatman No. 1) to remove residual polymer. Dye colorant could be added to the alcoholic monomer solution as an indicator. Standard organic solvent based dyes were added at 2 drops per ml. The solution was slightly warmed The solution (TDA/PDA) was filtered (Whatman No. 1) to remove residual polymer Dye colorant could be added to the alcoholic monomer solution as an indicator were added at 2 drops per ml

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,2;3,4-di-O-isopropylidene-D-galactopyranose (2.6 g, 10 mmol) and 10,12-tricosadiynoic acid (3.5 g, 10 mmol) were dissolved in 25 ml methylene chloride. 1-Ethyl-3(3-dimethylaminopropyl)carbodiimide (2 g, >10 mmol) was added neat. The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted to 100 ml, extracted with water (2×25 ml), dried over MgSO4 and the solvent was removed in vacuo. The crude product was treated with trifluoroacetic acid (10 ml) at room temperature for 30 minutes, evaporated in vacuo, and purified by straight phase chromatography on a CHROMATOTRON, eluted with methanol/chloroform (5:95). The product was characterised by NMR. The reaction mixture was diluted to 100 ml extracted with water (2×25 ml) dried over MgSO4 the solvent was removed in vacuo The crude product was treated with trifluoroacetic acid (10 ml) at room temperature for 30 minutes evaporated in vacuo purified by straight phase chromatography on a CHROMATOTRON eluted with methanol/chloroform (5:95)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-Amino-1-deoxy-β-D-galactose (180 mg, 1 mmol), and Fmoc-Lys(Boc)-OPfp (650 mg, 1 mmol) were dissolved in 4 ml dry dimethylformamide and stirred at room temperature overnight. The solvent was removed in vacuo, the residue was redissolved in acetonitrile/water (1:1), filtered and purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35). The relevant fractions were collected, concentrated in vacuo, and the product was characterised by NMR. The purified product (1 g, 1 mmol), 10,12-tricosadiynoic acid (350 mg, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide are dissolved in 10 ml dry dimethylformamide and stirred at room temperature overnight. The solvent is removed in vacuo, the residue redissolved in chloroform/methanol (95:5), filtered and purified by straight phase chromatography on a CHROMATOTRON. The relevant fractions are collected, concentrated in vacuo, and the product is characterised by NMR. The protecting groups of the α-ε amino groups are removed by standard reactions. Boc is removed by treatment with trifluoroacetic acid/methylene chloride for 30 minutes. The solvent is removed in vacuo. Fmoc is removed by treating the residue with 20% piperidine in dimethylformamide for 30 minutes, and the solvent is removed in vacuo. The final product is purified by reversed phase chromatography (Lobar RPSB). The solvent was removed in vacuo the residue was redissolved in acetonitrile/water (1:1) filtered purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35) The relevant fractions were collected concentrated in vacuo stirred at room temperature overnight The solvent is removed in vacuo the residue redissolved in chloroform/methanol (95:5) filtered purified by straight phase chromatography on a CHROMATOTRON The relevant fractions are collected concentrated in vacuo The protecting groups of the α-ε amino groups are removed by standard reactions Boc is removed by treatment with trifluoroacetic acid/methylene chloride for 30 minutes The solvent is removed in vacuo Fmoc is removed by treating the residue with 20% piperidine in dimethylformamide for 30 minutes the solvent is removed in vacuo The final product is purified by reversed phase chromatography (Lobar RPSB)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-Amino-1-deoxy-β-D-galactose (180 mg, 1 mmol), and Fmoc-Lys(Boc)-OPfp (650 mg, 1 mmol) were dissolved in 4 ml dry dimethylformamide and stirred at room temperature overnight. The solvent was removed in vacuo, the residue was redissolved in acetonitrile/water (1:1), filtered and purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35). The relevant fractions were collected, concentrated in vacuo, and the product was characterised by NMR. The purified product (1 g, 1 mmol), 10,12-tricosadiynoic acid (350 mg, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide are dissolved in 10 ml dry dimethylformamide and stirred at room temperature overnight. The solvent is removed in vacuo, the residue redissolved in chloroform/methanol (95:5), filtered and purified by straight phase chromatography on a CHROMATOTRON. The relevant fractions are collected, concentrated in vacuo, and the product is characterised by NMR. The protecting groups of the α-ε amino groups are removed by standard reactions. Boc is removed by treatment with trifluoroacetic acid/methylene chloride for 30 minutes. The solvent is removed in vacuo. Fmoc is removed by treating the residue with 20% piperidine in dimethylformamide for 30 minutes, and the solvent is removed in vacuo. The final product is purified by reversed phase chromatography (Lobar RPSB). The solvent was removed in vacuo the residue was redissolved in acetonitrile/water (1:1) filtered purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35) The relevant fractions were collected concentrated in vacuo stirred at room temperature overnight The solvent is removed in vacuo the residue redissolved in chloroform/methanol (95:5) filtered purified by straight phase chromatography on a CHROMATOTRON The relevant fractions are collected concentrated in vacuo The protecting groups of the α-ε amino groups are removed by standard reactions Boc is removed by treatment with trifluoroacetic acid/methylene chloride for 30 minutes The solvent is removed in vacuo Fmoc is removed by treating the residue with 20% piperidine in dimethylformamide for 30 minutes the solvent is removed in vacuo The final product is purified by reversed phase chromatography (Lobar RPSB)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 10,12-Tricosadiynoic acid (3.0 g, 0.0084 mol), methanol (15 ml) and concentrated sulfuric acid (0.8 ml) were heated to reflux and stirred for 1 hour. The cooled mixture was taken up in ether (40 ml) and washed with 10% NaHCO3 (20 ml) and water (20 ml), and the organic phase was dried (MgSO4). Evaporation of the solvent gave 2.68 g (74%) of the title compound. 1H NMR (60 MHz, CDCl3): δ 0.98 (m, 3H, CH3CH2), 1.28. (m, 28H, CH2), 2.25 (m, 6H, CH2), 3.70 (s, 3H, CH3O). to reflux washed with 10% NaHCO3 (20 ml) and water (20 ml) the organic phase was dried (MgSO4) Evaporation of the solvent

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 10,12-tricosadiynoic acid (10 gm., GFS Chemicals) was dissolved in a solution containing 10 ml methanol (HPLC grade) and 10 ml chloroform (HPLC grade). The solution was stirred at room temperature and 10 drops of neat sulfuric acid was added drop wise. The solution was warmed to 100° F. for 2 hour. The reaction mixture was purified using column chromatography. The product (MeTDA) was dried using a Rotovap and the material stored in a chloroform solution. The solid form of MeTDA was very unstable to polymerization and therefore kept dissolved in organic solutions. Alcoholic solutions of MePDA and MeTDA: Solids MePDA or MeTDA were dissolved in reagent grade ethanol to a concentration of 150 mg/ml. A residual polymer was removed by filtration through Whatman No. 1 filter paper. The solutions were held at room temperature or slightly above (70-75° F.) to avoid crystallization or precipitation. The solution was warmed to 100° F. for 2 hour The reaction mixture was purified The product (MeTDA) was dried The solid form of MeTDA was very unstable to polymerization kept dissolved in organic solutions A residual polymer was removed by filtration through Whatman No 1 filter paper were held at room temperature or slightly above (70-75° F.) crystallization or precipitation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 10,12-tricosadiynoic acid (10 gm, GFS Chemicals) was dissolved in a solution containing 10 ml methanol (HPLC grade) and 10 ml chloroform (HPLC grade). The solution was stirred at room temperature and 10 drops of neat sulfuric acid was added drop wise. The solution was warmed to 100° F. for 2 hour. The reaction mixture was purified using column chromatography. The product (MeTDA) was dried using a rotovap and the material stored in a chloroform solution. The solid form of MeTDA was very unstable to polymerization and therefore kept dissolved in organic solutions. Alcoholic solutions of MePDA and MeTDA: Solids MePDA or MeTDA were dissolved in reagent grade ethanol to a concentration of 150 mg/ml. An residual polymer was removed by filtration through Whatman No. 1 filter paper. The solutions was held at room temperature or slightly above (70-75° F.) to avoid crystallization or precipitation. The solution was warmed to 100° F. for 2 hour The reaction mixture was purified The product (MeTDA) was dried The solid form of MeTDA was very unstable to polymerization kept dissolved in organic solutions An residual polymer was removed by filtration through Whatman No 1 filter paper was held at room temperature or slightly above (70-75° F.) crystallization or precipitation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 10,12-tricosadiynoic acid (10 gm, GFS Chemicals) was dissolved in a solution containing 10 ml methanol (HPLC grade) and 10 ml chloroform (HPLC grade). The solution was stirred at room temperature and 10 drops of neat sulfuric acid was added drop wise. The solution was warmed to 100° F. for 2 hour. The reaction mixture was purified using column chromatography. The product (MeTDA) was dried using a rotovap and the material stored in a chloroform solution. The solid form of MeTDA was very unstable to polymerization and therefore kept dissolved in organic solutions. Alcoholic solutions of MePDA and MeTDA: Solids MePDA or MeTDA were dissolved in reagent grade ethanol to a concentration of 150 mg/ml. An residual polymer was removed by filtration through Whatman No. 1 filter paper. The solutions was held at room temperature or slightly above (70-75° F.) to avoid crystallization or precipitation. The solution was warmed to 100° F. for 2 hour The reaction mixture was purified The product (MeTDA) was dried The solid form of MeTDA was very unstable to polymerization kept dissolved in organic solutions An residual polymer was removed by filtration through Whatman No 1 filter paper was held at room temperature or slightly above (70-75° F.) crystallization or precipitation