3-[(2-methylpropan-2-yl)oxy]propane-1,2-diol

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

Procedure: Compound 25 was prepared using a method similar to that described for 23. The o reagents used were as follows, compound 17 (25.5 g, 0.172 mol.), compound 19 (91.5 g, 0.336 mol.), sodium hydride (60% by wt. in mineral oil (14.0 g, 0.350 mol.). The final product was a colorless liquid (30.0 g 60%) (bpt. 100°-120 0° C., 0.06 torr.): 1H-NMR (CDCl3), d (ppm) 3.8-3.4 (m, 17H), 1.55 (m, 4H, CH2), 1.2 (s, 9H, C(CH3)3), 0.9 (t, 6H, --CH3). Mass spectroscopy, m/e 349 MH+. Compound 25 was prepared a colorless liquid (30.0 g 60%) (bpt. 100°-120 0° C., 0.06 torr.)

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

Procedure: Compound 21 (31.0 g, 0.135 mol.) was added to a slurry of the di-sodium salt of 3-tert-butoxy-1,2-propane diol, (0.062 mol.), 17, in refluxing in dry THF (500 ml). The reaction mixture was stirred, heated and maintained at reflux under an atmosphere of dry nitrogen for 24 hours. The mixture was allowed to cool and filtered and the solvent was removed by evaporation under vacuum. The residue was extracted with chloroform, dried (MgSO4) filtered and solvent removed by vacuum rotary evaporation to yield a brown liquid (17.0 g). The crude product was washed with water (250 ml) and extracted with chloroform (300 ml). The organic fraction was separated from the aqueous and dried (MgSO4) filtered. The solvent was removed by rotary evaporation under vacuum to give a pale yellow oil (15.0 g, 94%). The crude product was distilled (bpt. 120°-125° C., 0.25 torr) to give a colorless oily liquid (11.1 g, 67%): IR 2975, 2875 (CH) cm-1, 1198 (COC) cm-1, 1108 (COC) cm-1, 1H-NMR (CDCl3), d (ppm) 3.3-3.85 (m, 19H), 1.3 (s, 9H, tert-butyl), 13C-NMR (CDCl3), d, (ppm) 78.95, 72.94, 72.21, 71.92, 71.74, 70.64, 69.69, 61.73, 58.98, 58.8, 27.43. Mass spectroscopy, m/e: 264 M+ ; 208 (M-C(CH3)3)+ base peak. heated maintained at reflux under an atmosphere of dry nitrogen for 24 hours to cool filtered the solvent was removed by evaporation under vacuum The residue was extracted with chloroform dried (MgSO4) filtered solvent removed by vacuum rotary evaporation

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

Procedure: Compound 21 (31.0 g, 0.135 mol.) was added to a slurry of the di-sodium salt of 3-tert-butoxy-1,2-propane diol, (0.062 mol.), 17, in refluxing in dry THF (500 ml). The reaction mixture was stirred, heated and maintained at reflux under an atmosphere of dry nitrogen for 24 hours. The mixture was allowed to cool and filtered and the solvent was removed by evaporation under vacuum. The residue was extracted with chloroform, dried (MgSO4) filtered and solvent removed by vacuum rotary evaporation to yield a brown liquid (17.0 g). The crude product was washed with water (250 ml) and extracted with chloroform (300 ml). The organic fraction was separated from the aqueous and dried (MgSO4) filtered. The solvent was removed by rotary evaporation under vacuum to give a pale yellow oil (15.0 g, 94%). The crude product was distilled (bpt. 120°-125° C., 0.25 torr) to give a colorless oily liquid (11.1 g, 67%): IR 2975, 2875 (CH) cm-1, 1198 (COC) cm-1, 1108 (COC) cm-1, 1H-NMR (CDCl3), d (ppm) 3.3-3.85 (m, 19H), 1.3 (s, 9H, tert-butyl), 13C-NMR (CDCl3), d, (ppm) 78.95, 72.94, 72.21, 71.92, 71.74, 70.64, 69.69, 61.73, 58.98, 58.8, 27.43. Mass spectroscopy, m/e: 264 M+ ; 208 (M-C(CH3)3)+ base peak. heated maintained at reflux under an atmosphere of dry nitrogen for 24 hours to cool filtered the solvent was removed by evaporation under vacuum The residue was extracted with chloroform dried (MgSO4) filtered solvent removed by vacuum rotary evaporation

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

Procedure: Compound 17 was prepared by the method described by Montanari and Tundo (Montanari, F. and Tundo, P., J. Org. Chem. 1982, 47, 1298). tert-Butyl glycidyl ether (Aldrich), (141 ml, 1.0 mol.) was added dropwise to 99% formic acid (83 ml, 2.2 mol). The reaction mixture was stirred and the temperature was maintained below 30° C. The mixture was stirred at room temperature for 12 hours. A solution of sodium hydroxide (100 g, 2.5 mol.) in 125 ml of water was added slowly, keeping the temperature below 40° C. The organic fraction was separated and the aqueous phase was extracted several times with dichloromethane. The combined organic fractions were dried (MgSO4) and evaporated and the oily residue was distilled under vacuum to give 17 (75 g, 54%) as a colorless oil: (bpt. 55°-60° C., 0.015 torr): IR 3400 (OH) cm-1 ; 1H-NMR (CDCl3) d (ppm) 3.25-4.0 (m, 7H), 1.2 (s, 9H); 13C-NMR (CDCl3) d (ppm) 73.5, 70.5, 64.4, 63.6, and 27.16. Mass spectrosocopy, m/e: 148 M+ base peak (Scheme 3). ##STR5## Compound 17 was prepared by the method the temperature was maintained below 30° C The mixture was stirred at room temperature for 12 hours the temperature below 40° C The organic fraction was separated the aqueous phase was extracted several times with dichloromethane The combined organic fractions were dried (MgSO4) evaporated the oily residue was distilled under vacuum

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

Procedure: Compound 25 was prepared using a method similar to that described for 23. The o reagents used were as follows, compound 17 (25.5 g, 0.172 mol.), compound 19 (91.5 g, 0.336 mol.), sodium hydride (60% by wt. in mineral oil (14.0 g, 0.350 mol.). The final product was a colorless liquid (30.0 g 60%) (bpt. 100°-120 0° C., 0.06 torr.): 1H-NMR (CDCl3), d (ppm) 3.8-3.4 (m, 17H), 1.55 (m, 4H, CH2), 1.2 (s, 9H, C(CH3)3), 0.9 (t, 6H, --CH3). Mass spectroscopy, m/e 349 MH+. Compound 25 was prepared a colorless liquid (30.0 g 60%) (bpt. 100°-120 0° C., 0.06 torr.)

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

Procedure: Compound 21 (31.0 g, 0.135 mol.) was added to a slurry of the di-sodium salt of 3-tert-butoxy-1,2-propane diol, (0.062 mol.), 17, in refluxing in dry THF (500 ml). The reaction mixture was stirred, heated and maintained at reflux under an atmosphere of dry nitrogen for 24 hours. The mixture was allowed to cool and filtered and the solvent was removed by evaporation under vacuum. The residue was extracted with chloroform, dried (MgSO4) filtered and solvent removed by vacuum rotary evaporation to yield a brown liquid (17.0 g). The crude product was washed with water (250 ml) and extracted with chloroform (300 ml). The organic fraction was separated from the aqueous and dried (MgSO4) filtered. The solvent was removed by rotary evaporation under vacuum to give a pale yellow oil (15.0 g, 94%). The crude product was distilled (bpt. 120°-125° C., 0.25 torr) to give a colorless oily liquid (11.1 g, 67%): IR 2975, 2875 (CH) cm-1, 1198 (COC) cm-1, 1108 (COC) cm-1, 1H-NMR (CDCl3), d (ppm) 3.3-3.85 (m, 19H), 1.3 (s, 9H, tert-butyl), 13C-NMR (CDCl3), d, (ppm) 78.95, 72.94, 72.21, 71.92, 71.74, 70.64, 69.69, 61.73, 58.98, 58.8, 27.43. Mass spectroscopy, m/e: 264 M+ ; 208 (M-C(CH3)3)+ base peak. heated maintained at reflux under an atmosphere of dry nitrogen for 24 hours to cool filtered the solvent was removed by evaporation under vacuum The residue was extracted with chloroform dried (MgSO4) filtered solvent removed by vacuum rotary evaporation

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

Procedure: Compound 17 was prepared by the method described by Montanari and Tundo (Montanari, F. and Tundo, P., J. Org. Chem. 1982, 47, 1298). tert-Butyl glycidyl ether (Aldrich), (141 ml, 1.0 mol.) was added dropwise to 99% formic acid (83 ml, 2.2 mol). The reaction mixture was stirred and the temperature was maintained below 30° C. The mixture was stirred at room temperature for 12 hours. A solution of sodium hydroxide (100 g, 2.5 mol.) in 125 ml of water was added slowly, keeping the temperature below 40° C. The organic fraction was separated and the aqueous phase was extracted several times with dichloromethane. The combined organic fractions were dried (MgSO4) and evaporated and the oily residue was distilled under vacuum to give 17 (75 g, 54%) as a colorless oil: (bpt. 55°-60° C., 0.015 torr): IR 3400 (OH) cm-1 ; 1H-NMR (CDCl3) d (ppm) 3.25-4.0 (m, 7H), 1.2 (s, 9H); 13C-NMR (CDCl3) d (ppm) 73.5, 70.5, 64.4, 63.6, and 27.16. Mass spectrosocopy, m/e: 148 M+ base peak (Scheme 3). ##STR5## Compound 17 was prepared by the method the temperature was maintained below 30° C The mixture was stirred at room temperature for 12 hours the temperature below 40° C The organic fraction was separated the aqueous phase was extracted several times with dichloromethane The combined organic fractions were dried (MgSO4) evaporated the oily residue was distilled under vacuum