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Xylose as raw material 3 - branching sugar Derivatives

Author: SunHePing
Tutor: LiuHongMin
School: Zhengzhou University
Course: Medicinal Chemistry
Keywords: 3-keto sugars of D-xylose branched sugar amino sugar imidazolinium compounds synthesis
CLC: R914
Type: Master's thesis
Year: 2007
Downloads: 42
Quote: 0
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Abstract


In this thesis, the main results obtained are as follows:1. Seven new 3-C-branched ribo- furanoses were stereoselectively synthesized with high yield by the reactions of the nucleophilic reagents (nitromethane, nitroethane, diethyl malonate, dimethyl malonate) with compound 1 or 7, the absolute configurations of compound 2 were confirmed by the X-ray crystallographic analysis of 2.2. Catalytic hydrogenation reaction was carried out under various conditions to give the branched amino sugar 11 and benzoyl transfered derivative 12 from 2, and the structure of 12 was elucidated by its X-ray crystallographic analysis and spectroscopic method. Some alkyl derivatives were synthesized in the presence of acid via an addition and reduction reaction in one-pot using 11 as material. This method offers an effective mean to synthesis amino augar derivations.3. In the presence of DCC as a dehydration reagent, some higher fatty acid amides derivatives and higher fatty acyl derivatives were obtained by the reaction of compounds 11 or 12 with higher fatty acids, and two diacyl derivatives were obtained respectively. 4. 3,6’-(2-amino) thiazine derivative 28 was stereoselectively synthesized by the reaction of keto- sugar 7 with thioureas. The method is a mild, simple, high stereo-selective method. The structure of 28 was confirmed by its X-ray crystallographic analysis and spectroscopic method.In the presence of DCC, compound 29 and 30 were obtained respectively by the reaction of compounds 28 with acetic acid and succinic acid.In the presence of DCC, three higher fatty acid monoamides derivatives (32,34,36) and two higher fatty acid diamides derivatives (31, 33, 35) were obtained by the reaction of compounds 28 with higher fatty acid. In conclusion, in this study 32 new compounds were synthesized and characterized by 1H NMR, 13C NMR, HRMS and IR spectra. The stereochemistry of three compounds among them was confirmed by X-ray crystallographic analyses.The inhibitory activity of some compounds to T-lymphocyte proliferation were tested.

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