1-iodooctadecane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diamino-9-(β-D-ribofuranosyl)purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 l) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solvent was evaporated and the residue purified by silica gel chromatography. The product was eluted with 5% MeOH/CH2Cl2. The product containing fraction were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH2); 1.22 [m, 32, O--CH2 --CH2 --(CH2)16 --]; 1.86 (m, 2, O--CH2CH2 --); 3.25 (m, 2, O--CH2 --); 3.93 (d, 1, 4'H), 4.25 (m, 1, 3'H); 4.38 (t, 1, 2'H); 5.08 (d, 1, 3'-OH); 5.48 (t, 1, 5'-OH); 5.75 (s, 2, 6-NH2); 5.84 (d, 1, 1'-H); 6.8 (s, 2, 2-NH2); and 7.95 (s, 1, 8-H). The solvent was evaporated the residue purified by silica gel chromatography The product was eluted with 5% MeOH/CH2Cl2 The product containing fraction were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diamino-9-(β-D-ribofuranosyl) purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 L) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solvent was evaporated and the residue purified by silica gel chromatography. The product was eluted with 5% MeOH/CH2Cl2. The appropriate fractions were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH2), 1.22 (m, 32, O-CH2 --CH2 --(CH2)16), 1.86 (m, 2, O-CH2CH2), 3.25 (m, 2, O-CH2), 3.93 (d, 1, 4'H), 4.25 (m, 1,3'H), 4.38 (t, 1,2'H), 5.08 (d, 1, 3'-OH), 5.48 (t, 1,5'-OH), 5.75 (s, 2,6-NH2), 5.84 (d, 1, 1'-H), 6.8 (s, 2,2-NH2), and 7.95 (s, 1,8-H). The solvent was evaporated the residue purified by silica gel chromatography The product was eluted with 5% MeOH/CH2Cl2 The appropriate fractions were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diamino-9-(β-D-ribofuranosyl)purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 L) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solyent was evaporated and the residue purified by silica gel chromatography. The product was eluted with 5% MeOH/CH2Cl2. The appropriate fractions were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH2), 1.22 (m, 32, O--CH2 --CH2 --(CH2)16), 1.86 (m, 2, O--CH2CH2), 3.25 (m, 2, O--CH2), 3.93 (d, 1, 4'H), 4.25 (m, 1, 3'H), 4.38 (t, 1, 2' H), 5.08 (d, 1, 3'-OH), 5.48 (t, 1, 5'-OH, 5.75 (s, 2, 6-NH2), 5.84 (d, 1, 1'-H), 6.8 (s, 2, 2-NH2), and 7.95 (s, 1, 8-H). The solyent was evaporated the residue purified by silica gel chromatography The product was eluted with 5% MeOH/CH2Cl2 The appropriate fractions were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diamino-9-(β-D-ribofuranosyl)purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 l) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solvent was evaporated and the residue purified by silica gel chromatography. The product was eluted with 5% MeOH/CH2Cl2. The product containing fraction were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ0.84 (t, 3, CH2); 1.22 [m, 32, O--CH2 --CH2 --(CH2)16 --]; 1.86 (m, 2, O--CH2CH2 --); 3.25 (m, 2, O--CH2 --); 3.93 (d, 1, 4'H), 4.25 (m, 1, 3'H); 4.38 (t, 1, 2'H); 5.08 (d, 1, 3'-OH); 5.48 (t, 1, 5'-OH); 5.75 (s, 2, 6-NH2); 5.84 (d, 1, 1'-H); 6.8 (s, 2, 2-NH2); and 7.95 (s, 1, 8-H). The solvent was evaporated the residue purified by silica gel chromatography The product was eluted with 5% MeOH/CH2Cl2 The product containing fraction were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diamino-9-(β-D-ribofuranosyl)purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 l) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solvent was evaporated and the residue purified by silica gel chromatography. The product was eluted with 5% MeOH/CH2Cl2. The product containing fraction were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH2); 1.22 [m, 32, O--CH2 --CH2 --(CH2)16 --]; 1.86 (m, 2, O--CH2CH2 --); 3.25 (m, 2, O--CH2 --); 3.93 (d, 1, 4'H), 4.25 (m, 1, 3'H); 4.38 (t, 1, 2'H); 5.08 (d, 1, 3'-OH); 5.48 (t, 1, 5'-OH); 5.75 (s, 2, 6-NH2); 5.84 (d, 1, 1'-H); 6.8 (s, 2, 2-NH2); and 7.95 (s, 1, 8-H). The solvent was evaporated the residue purified by silica gel chromatography The product was eluted with 5% MeOH/CH2Cl2 The product containing fraction were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diamino-9-(β-D-ribofuranosyl)purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 l) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solvent was evaporated and the residue purified by silica gel chromatography. The product was eluted with 5% MeOH/CH2Cl2. The product containing fraction were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH2); 1.22 [m, 32, O--CH2 --CH2 --(CH2)16 --]; 1.86 (m, 2, O--CH2CH2 --); 3.25 (m, 2, O--CH2 --); 3.93 (d, 1, 4'H), 4.25 (m, 1, 3'H); 4.38 (t, 1, 2'H); 5.08 (d, 1, 3'-OH); 5.48 (t, 1, 5'-OH); 5.75 (s, 2, 6-NH2); 5.84 (d, 1, 1'-H); 6.8 (s, 2, 2-NH2); and 7.95 (s, 1, 8-H). The solvent was evaporated the residue purified by silica gel chromatography The product was eluted with 5% MeOH/CH2Cl2 The product containing fraction were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of about 10.85 g of N-[1-(hydroxymethyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]acetamide in about 240 ml of dry dimethylformamide was added dropwise to a suspension of about 3.12 g of about 50% sodium hydride (pre-washed with anhydrous ether). After stirring about one hour a solution of about 22.8 g of octadecyl iodide in about 150 ml of tetrahydrofuran was added, stirring was continued for about 24 hours, then the mixture was diluted with ether and washed with a minimum amount of brine. The organic layer was dried, the solvents evaporated and the crude material purified by chromatography on silica gel, eluting with ethyl acetate:hexane:ethanol (about 1:1:0.2), giving about 8 g of the desired title compound, mp 52°-55° C. was added washed with a minimum amount of brine The organic layer was dried the solvents evaporated the crude material purified by chromatography on silica gel eluting with ethyl acetate

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of about 34.35 g of isopropylcyclohexylamine in about 150 ml of tetrahydrofuran at about -20° C. was added about 156.89 ml of an about 1.55M n-butyllithium, at a rate so that the final temperature reached about 10° C. The solution was then cooled to about -70° C. and about 25 g of ethyl levulinate ethylene ketal was added dropwise. After about 15 minutes, the solution was warmed to about -30° C. and maintained at that temperature while it was added rapidly, dropwise to a stirred solution of about 80.44 g of octadecyl iodide in about 150 ml of dimethyl sulfoxide and about 50 ml of tetrahydrofuran at room temperature. This mixture was stirred overnight, the volatile solvents were removed and water was added. The resulting solid was collected by filtration and extracted with ether giving a solution and a solid. This solution and original filtrate were combined and extracted with ether. This ether extract was dried and the solvent removed giving an oil. This oil was subjected to HPLC, eluting with hexane:ether (about 9:1). The product band was collected and the solvent removed, giving about 30.76 g of the desired title compound as a solid, mp 33°-34° C. reached about 10° C the solution was warmed to about -30° C. maintained at that temperature while it the volatile solvents were removed water was added The resulting solid was collected by filtration extracted with ether giving a solution extracted with ether This ether extract was dried the solvent removed giving an oil eluting with hexane The product band was collected the solvent removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of about 26.07 g of washed about 50% sodium hydride in about 1000 ml of dimethylformamide was added about 90 g of 2-(benzyloxy)-1,3-propanediol with stirring under argon. An about 187.88 g portion of octadecyl iodide and about 150 ml of tetrahydrofuran were added and the thick mixture was stirred with a glass rod, and then with magnetic stirring for about 3 hours. Water was then added and the mixture was extracted with ether. The ether extract was washed with brine, dried and filtered through a pad of florisil. The solvent was removed and the residue chromatographed on florisil, eluting first with petroleum ether, then with about 10% ether in petroleum ether and finally eluting the product with about 30% ether in petroleum ether, giving about 73.3 g of the desired title compound as a waxy solid. the thick mixture was stirred with a glass rod with magnetic stirring for about 3 hours the mixture was extracted with ether The ether extract was washed with brine dried filtered through a pad of florisil The solvent was removed the residue chromatographed on florisil eluting first with petroleum ether with about 10% ether in petroleum ether and finally eluting the product with about 30% ether in petroleum ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diamino-9-(β-D-ribofuranosyl)purine (50 g, 180 mmol) and sodium hydride (7 g) in DMF (1 l) were heated to boiling for 2 hr. Iodooctadecane (100 g) was added at 150° C. and the reaction mixture allowed to cool to RT. The reaction mixture was stirred for 11 days at RT. The solvent was evaporated and the residue purified by silica gel. chromatography. The product was eluted with 5% MeOH/CH2Cl2. The product containing fraction were evaporated to yield the product (11 g). 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH2); 1.22 [m, 32, O—CH2—CH2—(CH2)16—]; 1.86 (m, 2, O—CH2CH2—); 3.25 (m, 2, OCH2—); 3.93 (d, 1, 4′H), 4.25 (m, 1, 3′H); 4.38 (t, 1, 2′H); 5.08 (d, 1, 3′—OH); 5.48 (t, 1, 5′—OH); 5.75 (s, 2,6—NH2); 5.84 (d, 1, 1′-H); 6.8 (s, 2, 2—NH2); and 7.95 (s, 1, 8-H). The solvent was evaporated the residue purified by silica gel The product was eluted with 5% MeOH/CH2Cl2 The product containing fraction were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 ml reactor equipped with an agitator and nitrogen-inlet, nitrogen gas was slowly influxed as 2,4-dinitrophenol (7.36 g, 0.04 mole) was dissolved in 50 ml of the reacting solvent of dimethylacetamide. While influxing nitrogen gas, K2CO3 (6.99 g, 0.05 mole), 1-iodooctadecane (19 g, 0.05 mole) was slowly added and refluxed for 48 hours. The mixture was precipitated in excess distilled water. Thereafter, the solid material so filtered was recrystalized to obtain 2,4-dinitro-octadecanoxy-benzene (DN-L-18O) with the yield of 72%. To a 250 ml reactor equipped with an agitator and nitrogen-inlet, nitrogen gas was slowly added refluxed for 48 hours The mixture was precipitated in excess distilled water Thereafter, the solid material so filtered was recrystalized

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 ml reactor equipped with an agitator and nitrogen-inlet, nitrogen gas was slowly influxed as 2,4-dinitrophenol (7.36 g, 0.04 mole) was dissolved in 50 ml of the reacting solvent of dimethylacetamide. While influxing nitrogen gas, K2CO3 (6.99 g, 0.05 mole), 1-iodooctadecane (19 g, 0.05 mole) was slowly added and refluxed for 48 hours. The mixture was precipitated in excess distilled water. Thereafter, the solid material so filtered was recrystalized to obtain 2,4-dinitro-octadecanoxy-benzene (DN-L-18O) with the yield of 72%. To a 250 ml reactor equipped with an agitator and nitrogen-inlet, nitrogen gas was slowly added refluxed for 48 hours The mixture was precipitated in excess distilled water Thereafter, the solid material so filtered was recrystalized