L-核糖的化學合成研究.pdf

1、天津大學碩士學位論文L核糖的化學合成研究姓名：祁世波申請學位級別：碩士專業(yè)：應(yīng)用化學指導教師：張衛(wèi)紅20070101ABSTRACTWithQ—DglucoseaSstartingmaterial，LriboseWaSsynthesizedbyninestepreactionssuchasacetoneprotection，PDC(pyridiniumdichromate)oxidationNaBH4reduction，acidsele

2、ctivehydrolysis，Nal04oxidativedegradation，aldehydegroupprotectionwithmethoxylamine，DDQ(2，3一dichloro5，6一dicyano1，4benzoquinone)thoroughhydrolysis—NaBIhreductionanddeoximationwithtitaniumtrichlorideParticularlyPDCoxidation

3、method，Nal04oxidativedegradationmethodandaldehydegroupprotectionwithmethoxylaminemethodwerestudiedintensivelyThehydroxylgroupprotectingreactionsofaDgluofuranoseWasstudiedTheisopropylidenationreactionofQDgluofuranosewasca

4、rriedtosynthesis12：5，6OdiisopropylideneaDgluofuranose(2)withacetoneconcH2S04system，bycrystallizationtheyieldwas38％HydroxylgroupstereostructureconversioninsugarWaSstudiedTheC一3positionhydroxylgroupstereostructureof2WaScon

5、vertedbyPDCAc20CH2C12oxidationandNaBIhreducfionThus12：5，6Odiisopropylidene—aDallofuranose(3)WaSsynthesized，twostepsoverallyieldwas70％ThepreparationmethodofPDCWasstudiedSelectivehydrolysisreactionofaDallofuranosederivativ

6、e3WasstudiedTheselectivehydrolysisreactionof3WaScarriedtosynthesize1—2Oisopropylidene—QDallofuranose(4)withdiluteH2S04CH30H，theyieldWaS922％Oxidativedegradationreactionof4WaSstudiedThehydrolysisproduct4wascarbondecreaSing

7、oxidatedwithNal04NaHC03H20systemThus1，20一isopropylidene—a—Dribopentodialdo一14furanose(5)wassynthesized，theyieldwas869％AldehydegroupprotectionreactionofaDribosederivative5wasstudiedThereactionwascarriedoutwithNH20HCH30Hsy

8、stem，CH3CH2SHHClsystemandNH20CH3CH30HsystemThemethoxylaminewasdeterminedasaldehydegroupprotectionreagentThus12oisopropylideneQDribopentodialdo1，4fumnose一0methyl—oxime(60)Wassynthesized，theyieldWaS736％Thoroughhydrolysisre

9、ductionreactionof60WaSstudiedThediversionwasconvertedbyDDQCH3CNthoroughhydrolysisandNaBI14reductionThusLribose一0一methyl—oxime(7c)Wassynthesized，twostepsoverallyieldwas79％Deoximationreactionoftheoxime7cwasstudiedpremilina