Safety of Methyl tetrahydrofuran-2-carboxylate. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Methyl tetrahydrofuran-2-carboxylate, is researched, Molecular C6H10O3, CAS is 37443-42-8, about A scalable chemoenzymic preparation of (R)-tetrahydrofuran-2-carboxylic acid. Author is Fujima, Yoshito; Hirayama, Yoshihiro; Ikunaka, Masaya; Nishimoto, Yukifumi.
To develop a practical scalable approach to (R)-tetrahydrofuran-2-carboxylic acid (I), a chiral building block for furopenem, enantioselective hydrolysis of its esters is explored: When Et (±)-tetrahydrofuran-2-carboxylate (II, 2 M, 288 g/L) is digested by an Aspergillus melleus protease {0.2% (w/v)} in a 1.5 M potassium phosphate buffer (pH 8) for 20 h, enantioselective hydrolysis proceeds with E = 60 to give I in 94.4% ee. On separation from the leftover antipodal (S)-II by partition, I is treated with dicyclohexylamine in Me Et ketone/methanol (5:1) to precipitate the crystalline salt that contains I of >99% ee in 22% overall yield from II.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics