Name: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone. Author is Zunszain, Patricia A.; Varela, Oscar.
Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (I)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (II) and L-glutamic acid (III) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from II. The other strategy, which starts from III, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (IV) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave I (40% overall yield from IV).
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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI