On December 1, 1995, Paquette, Leo A.; Bailey, Simon published an article.Related Products of 38838-06-1 The title of the article was Evaluation of D-Ribose as an Enantiopure Building Block for Construction of the C-Ring of Taxol and Its Congeners. And the article contained the following:
The enantiomerically pure (4S,5R)-4-[(Z)-2-iodovinyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane is shown to be readily available from D-ribose via a sequence involving zinc-promoted reductive unmasking of an aldehyde and homologation with (iodomethylene)triphenylphosphorane. The vinyl anion produced by halogen-metal exchange adds from the endo direction to an enantiopure ketone prepared from D-camphor. The resulting carbinol undergoes anionic oxy-Cope rearrangement and C-methylation with complete stereocontrol to set the appropriate C-3 stereochem. of taxol. Dihydroxylation of this intermediate brings about facile transannular hemiketalization. DIBAL-H reduction of this intermediate does not affect the hemiketal, but does reduce the acetonide regiospecifically. An unusual transannular hydride shift occurs during subsequent heating with dibutyltin oxide, as confirmed by x-ray crystallog. When transannular hemiketalization is skirted, hydroboration-oxidation of the side chain leads to an acetaldehyde which is notably prone to β-elimination. Treatment with potassium carbonate in methanol does eventuate in ring closure to give I via an aldol addition reaction, but only after methanol has been added in Michael fashion to the α,β-unsaturated aldehyde. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Related Products of 38838-06-1
The Article related to ribose enantiopure synthesis taxol ring, Terpenes and Terpenoids: Diterpenes (C20), Including Gibberellins, Retinoids, Quassinoids, and Tocopherols and other aspects.Related Products of 38838-06-1
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem