Imidazole → (5S,7S)-2-[5,7-bis-(tert-butyl-diphenyl-silanyloxy)-non-8-en-2-ynyloxy]-tetrahydropyran

Participants

Reaction Steps

10.40 g (40.9 mmol) of (3S,5S)-9-(tetrahydro-pyran-2-yloxy)-non-1-en-7-yne-3,5-diol was dissolved in 30 ml of abs. DMF and treated successively with 18.9 g (6.8 eq.) of imidazole and 35.5 ml (3.4 eq.) of tert-butyl-chlorodiphenylsilane. After stirring for 20 h at 40°, the reaction mixture was poured onto crushed ice/EtOEt. Usual workup followed by flash chromatography (SiO2, hexane/AcOEt=96/6) gave 25.16 g of (5S,7S)-2-[5,7-bis-(tert-butyl-diphenyl-silanyloxy)-non-8-en-2-ynyloxy]-tetrahydropyran as colorless oil (1:1 epimeric mixture).

Provenance & Evidence