Glucosamine 유도체의 입체선택적 합성(II): 5-(N-페닐카바모일메틸)-2-페닐이미노-티아졸리딘-4-온

Abstract

2-Amino-deoxy-D-glucopyranose glucosamine, a compound which is effective against degenerative arthrists, has usefulαglucosamine is superior to β-glucosamine when it comes to physiologicalactivity. This leads our team to manufacture only αglucosamine used as a starting material. Meanwhile, 5-(N-phenylcarbamoylmethyl)-2-phenylimino-thiazolidin-4-one, a heterocyclic compound, has the structural properties of highphysiological activity. Using each molecule of αglucosamine and 5-(N-phenylcarbamoylmethyl)-2-phenylimino-thiazolidin-4-one derivative, the study manufactured a new compound, α-D-glucopyranosyl phenylisothiocyanate-4-one. As a first step,phenylisothiocyanate was synthesized by reaction of aniline and thiophosgene. Secondly, N-(α-D-glucopyranosyl)-N'-phenylthiourea was gained by reaction of glucosamine and phenylisothiocyanate of which sterochemistry are fixed as alpha. Andtetra-O-acetyl-2-deoxy-2-(4-oxo-5-phenylcarbamoylmethyl-2-phenylimino-thiazolidin-3-yl)-α-D-glucopyranose 2 derivative bycombining N-(α-D-glucopyranosyl)-N'-phenylthiourea and 1-phenyl-pyrrole-2,5-dione. The created α-D-glucopyranosylphenyliminothiazolines-4-one was confirmed for the physical properties such as purity, yield, melting point and Rf value fordeveloping solvent. While 1H NMR was as that of a single compound in a solvent, CDCl3, it was found that in a solvent, DMSO-d6, it exists as diastereomer. The chemical shift of 1-H was a coupling constant(J), 3.5 Hz as doublet around 6.1 ppm, which waschemical evidence of stereospecific alpha-type as it appeared in the lowest area among 6 protons of pyranose ring.