Benzoyl chloride → 2,3,5-tri-O-benzoyl-1-O-methyl-L-ribofuranose

31.18 g of the crude 1-O-methyl-L-ribofuranose synthesized in (1) above, toluene (175 ml), a 25 wt. % sodium hydroxide aqueous solution (111 ml), and tetra-normal-butyl ammonium bromide (1.20 g; 5 molar % ratio) were added to a 1-L flask. The obtained mixture was cooled to an ice-cooled temperature, and benzoyl chloride (56.6 mol; 3.05 equivalents) was then slowly added dropwise thereto. The temperature was increased to room temperature, and the reaction was then carried out for 2 hours. The reaction product was again cooled to an ice-cooled temperature, and it was then diluted with toluene (200 ml) and a 1 N sodium hydroxide aqueous solution (100 ml). The temperature was increased to room temperature, and an organic layer was separated from an aqueous layer. The organic layer was washed with a 1 N sodium hydroxide aqueous solution (100 ml) 2 times, and was then washed with a 3 N hydrochloric acid aqueous solution (200 ml), so that the organic layer was concentrated. Thus, 62.69 g of crude 2,3,5-tri-O-benzoyl-1-O-methyl-L-ribofuranose was obtained in the form of a colorless oily liquid.

1. additionwas then slowly added dropwise
2. temperaturecooled temperature, and it
3. temperatureThe temperature was increased to room temperature
4. customan organic layer was separated from an aqueous layer
5. washThe organic layer was washed with a 1 N sodium hydroxide aqueous solution (100 ml) 2 times
6. washwas then washed with a 3 N hydrochloric acid aqueous solution (200 ml), so that the organic layer
7. concentrationwas concentrated

ORD record

ord-5156c256d0454c29817a915181febca6

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394935B2