Uracil → HCID 10670845, compound

Participants

Reaction Steps

Uracil is bis-trimethylsilylated according to the procedure of Niedballa and Vorbruggen. Uracil is dissolved in benzene, and added to 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose 33.1b (Xi=β--OAc) (Niedbala and Vorbruggen) in 1,2 dichloroethane followed by tin tetrachloride in 1,2-dichloroethane according to the method of Vorbruggen and Niedballa to provide the 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)uracil 33.1b (Xi=β-uracil-1-yl). Following methanolysis with sodium methoxide in methanol the 1-(β-D-glucopyranosyl)uracil 33.1a (Xi=β-uracil-1-yl) is obtained. This is converted into the morpholino subunit 32.2b (Xi=β-uracil-1-yl) by the general procedure.

Provenance & Evidence