HCID 14621461, compound → HCID 14621463, compound

A solution of (2R,4R,5S)-4-t-butyldimethylsiloxymethyl-5-ethoxycarbonylmethyl-2-methyl-1,3-dioxane (9.30 g) in toluene (93 ml) was cooled in a dry ice acetone bath and to the solution was added dropwise diisobutyl aluminum hydride (1.5 M solution in toluene, 26.4 ml). The mixture was stirred at the same temperature for 1 hour. After quenching the mixture with saturated aqueous ammonium chloride, to the solution was added a mixture of ethyl acetate (300 ml) and water (300 ml). Insoluble materials were filtered off. The filtrate was extracted with ethyl acetate and organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column (250 g) with a mixture of n-hexane and ethyl acetate (10:1) as an eluent to give (2R,4R,5S)-4-t-butyldimethylsiloxymethyl-5-formylmethyl -2-methyl-1,3-dioxane (6.61 g) as a colorless oil.

1. customAfter quenching the mixture with saturated aqueous ammonium chloride
2. additionto the solution was added
3. additiona mixture of ethyl acetate (300 ml) and water (300 ml)
4. filtrationInsoluble materials were filtered off
5. extractionThe filtrate was extracted with ethyl acetate and organic layer
6. washwas washed with brine
7. dry with materialdried over magnesium sulfate
8. customThe solvent was evaporated in vacuo
9. customthe residue was chromatographed on a silica gel column (250 g) with a mixture of n-hexane and ethyl acetate (10:1) as an eluent

ORD record

ord-748505fbcf6d492c8e38f934857e27db

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04929639