【摘要】 以D-氨基葡萄糖盐酸盐、三氯乙晴、三氯乙氧甲酰氯和三甲基硅三氟甲基磺酸酯(TMSOTF)为主要原料,合成了保护的氨基葡萄糖5,8,9,12,13和两种保护的2脱氧2氨基葡二糖10和11,它们均为新化合物。用1HNMR和13CNMR谱等进行了表征。所列核磁共振氢谱数据表明保护的氨基葡萄糖、保护的氨基葡二糖中的NH上质子化学位移(δ)显著地移向低场至507～526。9,10,11,12,13化合物中的J1,2值在72～88Hz,均为β糖苷;而J1,2值在300和496Hz,为α糖苷(5和6)。H2的化学位移一般处在较高场,δ在310～430。所列13C谱数据表明C1的化学位移处于最低场,C2处于较高场,相应的氢有类似情况。一般C1的δ>100(如化合物91019)为β苷;而δ<100(如化合物5δ=9520,化合物6δ=9721)为α糖苷。讨论了糖环上其他H和C的化学位移特征。用DEPT(DistortionlessEnhancementbyPolarizationTransfer)法配合13CNMR谱方便而清楚地鉴别了化合物6中碳原子的级数。更多还原

【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 13 C 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 J 1, 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 J 1, 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 13 C 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 13 C NMR.更多还原