Luppi Gianluigi, Villa Marzia, Tomasini Claudia
Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum, Università di Bologna, Via Selmi, 2-40126 Bologna, Italy.
Org Biomol Chem. 2003 Jan 21;1(2):247-50. doi: 10.1039/b210725m.
A four step synthesis of 4(S)-oxazolidineacetic acid, 2-oxo benzyl ester (D-Oxac-OBn) from L-Asp-OH in 45% overall yield is reported. The formation of by-products is completely avoided, by microwave irradiation and by the use of caesium carbonate as base. Moreover the synthesis and IR and 1H NMR conformational analysis of the tetramers Boc-L-Val-D-Oxac-L-Ala-OBn and Boc-L-Val-D-Oxac-Aib-L-Ala-OBn in solution is reported.
据报道，以L-天冬氨酸为原料，通过四步合成法可制得4(S)-恶唑烷乙酸2-氧代苄酯（D-Oxac-OBn），总产率为45%。通过微波辐射以及使用碳酸铯作为碱，可完全避免副产物的生成。此外，还报道了四聚体Boc-L-缬氨酸-D-Oxac-L-丙氨酸-OBn和Boc-L-缬氨酸-D-Oxac-Aib-L-丙氨酸-OBn在溶液中的合成及其红外光谱和1H核磁共振构象分析。
