| 光谱学与光谱分析 |
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| NMR Study on the Determination of Structure in the Protected Glucosamineoside |
| GUO Zhen-chu, HAN Liang, HU Bo, XIONG Xing-quan |
| Faculty of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China |
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Abstract The protected glucosamines 5,8,9,12,13 and the protected diglucosamines 10 and 11 were prepared from D-glucosamine hydrochloride, trichloroacetonitrile, trichlorocthoxycarbonyl chloride and trimethylsilyl trifluoromethanesulfonate(TMSOTf). They were new products and their structures were characterized by means of 1H NMR and 13C NMR. The data of 1H NMR indicated that the chemical shift of NH of them were moved remarkably to the low field 5.07-5.26 compared with that of D-glucosamine hydrochloride. The data J1, 2 of the compounds 9,10,11,12,13 were between 7.2 and 8.8 Hz, which showed their structures were β configuration, while the data J1, 2 were between 3.00 and 4.96 Hz in the compounds 5 and 6, which showed their structures were α configuration. H-2 was situated in the higher field, which δ was between 3.10 and 4.30. The data of 13C NMR showed that the δ of C-1 laid in the lowest field and the δ of C-2 laid in the higher field, as were the δ of H-1 and H-2 in NMR . Commonly speaking, if the δ of C-1 was greater than 100, the structure of the compound was β configuration such as compound 9 (δ=101.9). On the contrary, if the δ of C-1 was less than 100, the structures were α configuration like compound 5 (δ=95.20)and 6(δ=97.21) . The chemical shift of other carbon and hydrogen in the ring were discussed. The progression of Carbon in the compound 6 were distinguished conveniently and clearly by using DEPT (Distortionless Enhancement by Polarization Transfer)and 13C NMR.
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Received: 2003-12-06
Accepted: 2004-04-18
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Corresponding Authors:
HAN Liang
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| Cite this article: |
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GUO Zhen-chu,HAN Liang,HU Bo, et al. NMR Study on the Determination of Structure in the Protected Glucosamineoside[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2004, 24(11): 1476-1481.
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http://www.gpxygpfx.com/EN/Y2004/V24/I11/1476 |
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