1,16-HEXADECANEDIOL

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added acetone was removed in vacuum eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101

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

Procedure: To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added acetone was removed in vacuum eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101

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

Procedure: To a stirred solution of 4-hydroxy-benzaldehyde (0.24 g, 2mmol) and 1,16-dihydroxyhexadecane (0.51 g, 2 mmol), triphenylphosphine (0.53 g, 2 mmol) in dry THF (20 ml) at −15° C. under an argon atmosphere was added a solution of diisopropylazodicarboxylate (0.4 g, 2 mmol) in dry THF (7.5 ml) over a period of 40 minutes. The mixture was allowed to warm to room temperature overnight. The solvent was removed under reduced pressure, diethyl ether was added and the white solid formed was removed by filtration. The filtrate was evaporated to dryness and the residue purified by chromatography on a column of silica gel which was, eluted with petroleum ether (b.p. 40-60° C.):tetrahydrofuran (THF) (10:1 by volume) to yield the title compound which was used directly without further purification. The solvent was removed under reduced pressure, diethyl ether was added the white solid formed was removed by filtration The filtrate was evaporated to dryness the residue purified by chromatography on a column of silica gel which eluted with petroleum ether (b.p. 40-60° C.)

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

Procedure: To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of the compound of Structure 1 (C-101). After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added acetone was removed in vacuum eluted with pentane-ethyl acetate (2:1)

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

Procedure: To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of the compound of Structure 1 (C-101). After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added acetone was removed in vacuum eluted with pentane-ethyl acetate (2:1)

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

Procedure: Under an argon atmosphere, 16-Hexadecanolide (4.860 g, 18.5 mmol) in THF (80 mL) was added with stirring to a suspension of lithium aluminium hydride (1.280 g, 33.7 mmol, 1.8 eq.) in THF (160 mL) at 0° C. Stirring was continued at this temperature for 1 h and for 3 more hours at r.t. Potassium sodium tartrate solution was carefully dropped to this mixture with stirring. The phases were separated and the aqueous phase was extracted with diethyl ether (3×100 mL). The combined organic layer was dried over MgSO4. After evaporation of the solvent, the product was isolated as a white solid, which was used for the next step without purification. Yield: 4.598 g (96%). with stirring The phases were separated the aqueous phase was extracted with diethyl ether (3×100 mL) The combined organic layer was dried over MgSO4 After evaporation of the solvent the product was isolated as a white solid, which was used for the next step without purification

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

Procedure: Under an argon atmosphere, 16-Hexadecanolide (4.860 g, 18.5 mmol) in THF (80 mL) was added with stirring to a suspension of lithium aluminium hydride (1.280 g, 33.7 mmol, 1.8 eq.) in THF (160 mL) at 0° C. Stirring was continued at this temperature for 1 h and for 3 more hours at r.t. Potassium sodium tartrate solution was carefully dropped to this mixture with stirring. The phases were separated and the aqueous phase was extracted with diethyl ether (3×100 mL). The combined organic layer was dried over MgSO4. After evaporation of the solvent, the product was isolated as a white solid, which was used for the next step without purification. Yield: 4.598 g (96%). with stirring The phases were separated the aqueous phase was extracted with diethyl ether (3×100 mL) The combined organic layer was dried over MgSO4 After evaporation of the solvent the product was isolated as a white solid, which was used for the next step without purification

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

Procedure: To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added acetone was removed in vacuum eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101

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

Procedure: To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added acetone was removed in vacuum eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101

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

Procedure: To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added acetone was removed in vacuum eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101