Synthetic Route of C5H8O3. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about SmI2 promoted elimination in 5-O-silyl derivatives of D-ribono-1,4-lactone. Author is Zunszain, Patricia A.; Varela, Oscar.
Regioselective silylation of D-ribono-1,4-lactone with 1.1 molar equivalents of tert-butylchlorodiphenylsilane led to the 5-O-silyl derivative (72% yield). The free HO-2 and HO-3 were acetylated or benzoylated to give the products in almost quant. yield. The SmI2-promoted elimination of the 2,3-acyloxy groups was applied to these products. It was proven that the silyloxy group was stable under the reaction conditions, and the butenolide 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-glycero-pent-2-eno-1,4-lactone was obtained in over 50% yield. In order to establish its optical purity, the butenolide was hydrogenated and O-desilylated to the (S)-4-hydroxymethyl-1,4-butyrolactone. Alternatively, enantiomerically pure 4-hydroxymethyl-1,4-butyrolactone was prepared from L-glutamic acid. The optical rotations of 4-hydroxymethyl-1,4-butyrolactone from both preparations were very coincident, indicating high optical purity (ee > 05%) for the butenolide.
In addition to the literature in the link below, there is a lot of literature about this compound((S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one)Synthetic Route of C5H8O3, illustrating the importance and wide applicability of this compound(32780-06-6).
Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI