Dimethyl Sulfoxide → HCID 131729443, compound

Participants

Reaction Conditions

Reaction Steps

[(2S,3S,5R,6R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxan-2-yl]-methanol (prepared from dimethyl L-tartrate according to J. Chem. Soc. Perkin 1 (1999), 1635; 9.2 g, 19.4 mmol) was dissolved in DCM (100 mL) and cooled to 0° C. DIPEA (19.9 mL, 6 eq.) was added and a solution of Pyr.SO3 complex (6.17 g, 2 eq.) in DMSO (27.5 mL, 20 eq.) was added dropwise over 20 min. The mixture was stirred at 0° C. for 4 h, diluted with DCM (200 mL) and washed several times with water. The org. phase was dried over MgSO4 and concentrated. The title aldehyde was isolated after FC (Hept/EA 2:1) as a colourless oil (8.6 g, 94% yield).

Provenance & Evidence