(5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-one

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

Procedure: The title compound is prepared by the procedure of Example 353 using 0.868 g of product from Example 359, 10 ml of toluene and 0.763 g of Lawesson's Reagent to give 0.530 g of the desired product.

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

Procedure: The title compound is prepared by the procedure of Example 353 using 0.868 g of product from Example 359, 10 ml of toluene and 0.763 g of Lawesson's Reagent to give 0.530 g of the desired product.

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

Procedure: The title compound is prepared by the procedure of Example 353 using 0.868 g of product from Example 359, 10 ml of toluene and 0.763 g of Lawesson's Reagent to give 0.530 g of the desired product.

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

Procedure: A solution of 13.2 g (113 mmol) of (5S)-dihydro-5-(hydroxymethyl)furan-2(3H)-one in 200 ml of dimethyiformamide was treated sequentially with 9.28 g (136 mmol) of imidazole and 18.84 g (125 mmol) of chloro-t-butyldimethylsilane, the latter in several portions. The resulting solution was stirred at ambient temperature for 6 h, poured into 10% aqueous citric acid, and extracted with ethyl acetate. The organic layer was washed sequentially with two portions of water, one portion of aqueous NaHCO3 and one portion of saturated brine. The organic layer was dried over MgSO4, and concentrated in vacuo to provide 22.04 g (90%) of the desired compound. extracted with ethyl acetate The organic layer was washed sequentially with two portions of water, one portion of aqueous NaHCO3 and one portion of saturated brine The organic layer was dried over MgSO4 concentrated in vacuo

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

Procedure: A solution of 13.2 g (113 mmol) of (5S)-dihydro-5-(hydroxymethyl)furan-2(3H)-one in 200 ml of dimethyiformamide was treated sequentially with 9.28 g (136 mmol) of imidazole and 18.84 g (125 mmol) of chloro-t-butyldimethylsilane, the latter in several portions. The resulting solution was stirred at ambient temperature for 6 h, poured into 10% aqueous citric acid, and extracted with ethyl acetate. The organic layer was washed sequentially with two portions of water, one portion of aqueous NaHCO3 and one portion of saturated brine. The organic layer was dried over MgSO4, and concentrated in vacuo to provide 22.04 g (90%) of the desired compound. extracted with ethyl acetate The organic layer was washed sequentially with two portions of water, one portion of aqueous NaHCO3 and one portion of saturated brine The organic layer was dried over MgSO4 concentrated in vacuo

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

Procedure: The title compound is prepared by the procedure of Example 353 using 0.868 g of product from Example 359, 10 ml of toluene and 0,763 g of Lawesson's Reagent to give 0.530 g of the desired product.