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首页 羟基、氨基及氨基酸的各种保护基及去保护方法大全

羟基、氨基及氨基酸的各种保护基及去保护方法大全.pdf

羟基、氨基及氨基酸的各种保护基及去保护方法大全

asunchem
2011-11-30 0人阅读 举报 0 0 暂无简介

简介:本文档为《羟基、氨基及氨基酸的各种保护基及去保护方法大全pdf》,可适用于自然科学领域

醚、氨基及氨基酸的各种保护基及去保护方法大全(整理有详细操作)AcetateBenzoatelPivaloateLevulinateBacktoCarbSynthesisAc(acetate)esterStandardProtectionProcedureToasolutionoftheglycosideindrypyridine(eq)underaninertatmosphereatroomtemperature,aceticanhydride(eq)isaddedandstirreduntilcompletebyTLC(usuallyh)ThereactionmixtureisthenpouredintoicewaterandextractedthreetimeswithchloroformThecombinedorganiclayersareextractedwithHCl,saturatedaqueoussodiumbicarbonate,andwaterTheorganiclayeristhendriedandconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinmethanolandasolutionofsodiummethoxideinmethanol(eqperOAc)isaddeddropwiseat°ThesolutioniswarmedtoroomtemperatureandstirredunderaninertatmosphereuntilcompletebyTLC(usuallywithinafewhours)AmberlitecationicexchangeresinisthenaddedwithvigorousstirringuntilthepHofthemixtureisneutralThemixtureisthenfilteredandconcentratedTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryORTheGlycosideisdissolvedinmethanolandhydrazinehydrate(eqperOAc)isaddedintwoportionsoverhoursThesolutionisstirredatroomtemperatureunderaninertatmosphereuntilcompletebyTLC(usuallyhours)ThesolutionisthenneutralizedwithglacialaceticacidThemixtureisfilteredthroughceliteandconcentratedTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesJOrgChem,,,"SyntheticMethodsforCarbohydrates"Lemieux,Ch,pgJChemSoc,PerkinTrans,,Bz(benzoate)esterStandardProtectionProcedureToasolutionoftheglycosidedissolvedindrypyridine(M),benzoylchloride(eqperOH)isaddedatroomtemperatureunderaninertatmosphereandstirreduntilcompletebyTLC(usuallyh)MethanolisaddedandthesolutionwasconcentratedinvacuoTheresiduewasdissolvedinDCMandwashedwithwater,saturatedcoppersulfate,andbrineTheorganiclayerisdriedandconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinMeOHandasolutionofNaOH(eqperOH)inMeOHisaddedslowlyThemixtureisstirredatroomtemperatureunderaninertatmospheretillcompletebyTLC(usuallyh)andthenconcentratedinvacuoTheresidueisdissolvedinethylacetateandtheorganicsolutioniswashedtwicewithwater,dried(sodiumsulfate),andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesTetrahedron,,,CarbRes,,,Piv(pivaloate)esterStandardProcedureTheglycosideisdissolvedinpyridine:DCM:andcooledto°PivCl(eqperOH)isthenaddeddropwiseunderaninertatmosphereandtheresultisstirredat°untilcompletebyTLC(usuallyh)ThemixtureisthendilutedwithDCMandextractedwithHCltwiceandoncewithwaterTheorganiclayeristhendried(sodiumsulfate)andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinMeOH,andasolutionofsodiummethoxideinmethanol(eqperOH)isaddeddropwiseatroomtemperatureunderaninertatmosphereandstirreduntilthereactioniscompletebyTLC(usuallyh)AqueousHCl()isaddedtothesolutionuntilneutralandtheresultingmixtureisconcentratedinvacuoTheresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesTetAsym,JAmChemSoc,,Lev(levulinate)esterStandardProtectionProcedureToasolutionoftheglycosideindrypyridineatroomtemperatureunderaninertatmosphere,levulinicanhydride(eq)isaddeddropwiseThereactionwasstirreduntilcompletebyTLC(usuallyh)andicewaterisaddedThemixtureisextractedwithchloroformandthentheorganiclayerisbackextractedwithbrine,dried(sodiumsulfate),andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinpyridineandhydrazinehydrate(Minpyridine:aceticacid:)isaddedatroomtemperatureunderaninertatmosphereAfteradditionofhydrazineissufficienttoconsumestartingmaterialcompletelybyTLC(usuallyafewminutes),pentane,dioneisaddedwithcoolingtoquenchthereactionThemixtureisdilutedwithchloroformandextractedoncewithwaterandoncewithbrineTheorganiclayerisdried(sodiumsulfate)andconcentratedinvacuoTheresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesJACS,,,TetLett,,,BenzylTritylPMPAllylpMBBacktoCarbSynthesisBn(benzyl)etherStandardProtectionProcedureToasolutionofsodiumhydride(eqperOH)inDMF,theglycoside(dissolvedinDMF)isaddeddropwiseat°underaninertatmosphereThemixtureisstirredforminutesat°andbenzylbromide(eqperOH)isaddeddropwise*NoteacatalyticamountofTBAIorcrownethercanbeaddedThereactionisstirredatroomtemperatureuntilcompletebyTLC(usuallyh)andmethanolisaddedslowlytoquenchthereactionThesolutionisthendilutedwithchloroformandwater,extractedtimeswithwaterandoncewithbrineTheorganiclayerisdried(sodiumsulfate)andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryORToasolutionoftheglycosideinDCM,benzyltrichloroacetimidate(eqperOH)isaddeddropwise(asasolutionincyclohexaneseethirdreference)withTfOH(catalytic>mol)TheresultisstirredatroomtemperatureunderinertatmosphereuntilcompletebyTLC(usuallyovernight)SaturatedaqueoussodiumbicarbonateisaddedandthemixtureisdilutedwithDCMTheorganiclayerisextractedoncewithwater,oncewithbrine,dried(sodiumsulfate),andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedin:MeOH:tBuOHandpalladiumhydroxide(eq)isaddedatroomtemperatureAhydrogenatmosphereisadded(balloonpressure)andthereactionisstirreduntilcompletebyTLC(usuallyh)Themixtureisthenfilteredandconcentrated*Notecatalyticglacialacidicacidmaybeaddedifthereactionisn'tcompleteTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesJOrgChem,,,JAmChemSoc,,,Tr(triphenylmethyl)ortrityletherStandardProtectionProcedureToasolutionoftheglycoside,tritylchloride(eqforprimaryoversecondary,eqforeachOHotherwise),andtriethylamine(eqforprimaryoversecondary,eqforeachOHotherwise)stirringinDMFunderaninertatmosphereatroomtemperature,DMAP(eq)isaddedThereactionisstirreduntilcompletebyTLC(usuallyovernight)andthenpouredintoicewaterThemixtureisextractedwithchloroformandtheorganiclayeriswashedwithsaturatedaqueousammoniumchlorideandwater,dried(sodiumsulfate),andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinethanolandpalladiumoncharcoalisaddedunderahydrogenatmosphereThereactionisstirreduntilcompletebyTLC(usuallyovernight)andfilteredThesolutionisconcentratedandtheresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesTetLett,,,JOC,,,pMB(paramethoxybenzyl)etherStandardProtectionProcedureToasolutionofsodiumhydride(eqperOH)inDMF,theglycoside(dissolvedinDMF)isaddeddropwiseat°underaninertatmosphereThemixtureisstirredforminutesat°andparamethoxybenzylbromide(eqperOH)isaddeddropwise*NoteacatalyticamountofTBAIorcrownethercanbeaddedThereactionisstirredatroomtemperatureuntilcompletebyTLC(usuallyh)andmethanolisaddedslowlytoquenchthereactionThesolutionisthendilutedwithchloroformandwater,extractedtimeswithwaterandoncewithbrineTheorganiclayerisdried(sodiumsulfate)andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinDCMHO:andDDQ(uptoeq)isaddedatroomtemperatureunderaninertatmosphereThereactionisstirreduntilcompletebyTLC(usuallyh,mayrequireheat)anddilutedwithDCMThesolutionisextractedwithsaturatedaqueoussodiumbicarbonate,dried(sodiumsulfate),andconcentratedinvacuoProductcanthenbepurifiedbycolumnchromatographyifnecessaryTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesJACS,,,JACS,,,Allyl(allyl)etherStandardProtectionProcedureToasolutionofsodiumhydride(eqperOH)inDMF,theglycoside(dissolvedinDMF)isaddeddropwiseat°underaninertatmosphereThemixtureisstirredforminutesat°andallybromide(eqperOH)isaddeddropwise*NoteacatalyticamountofTBAIorcrownethercanbeaddedThereactionisstirredatroomtemperatureuntilcompletebyTLC(usuallyh)andmethanolisaddedslowlytoquenchthereactionThesolutionisthendilutedwithchloroformandwater,extractedtimeswithwaterandoncewithbrineTheorganiclayerisdried(sodiumsulfate)andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryORToasolutionoftheglycosideinDCM,benzyltrichloroacetimidate(eqperOH)isaddeddropwise(asasolutionincyclohexaneseethirdreference)withTfOH(catalytic>mol)TheresultisstirredatroomtemperatureunderinertatmosphereuntilcompletebyTLC(usuallyovernight)SaturatedaqueoussodiumbicarbonateisaddedandthemixtureisdilutedwithDCMTheorganiclayerisextractedoncewithwater,oncewithbrine,dried(sodiumsulfate),andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinAcOH:water:andPalladiumchloride(eq)followedbysodiumacetate(eq)isaddedThemixtureisstirredunderaninertatmosphereatroomtemperatureuntilcompletebyTLC(usuallyovernight)EthylacetateisaddedandthemixtureisextractedtimeswithsaturatedaqueoussodiumbicarbonateTheorganiclayeristhenextractedoncewithbrine,dried(sodiumsulfate),andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesTetLett,,,,,JOC,,,JChemSocPerkinTransI,,JACS,,,PMP(pmethoxyphenyl)etherStandardProtectionProcedureToasolutionoftheglycosideinTHFunderaninertatmosphereisaddedtriphenylphosphine(eq),diethylazocarboxylate(eq),andpmethoxyphenol(eq)Theresultingsolutionisheatedto°andstirreduntilcompletebyTLC(usuallyh)Themixtureisconcentratedinvacuoandpurifiedbyflashchromatography(SiO)RemovalTheglycosideisdissolvedinacetonitrile:water:atroomtemperatureunderaninertatmosphereandCAN(eq)isaddedThemixtureisstirreduntilcompletebyTLC(usuallylessthanh)anddilutedwithchloroformTheresultingsolutioniswashedwithwaterandsaturatedsodiumchloridesolutionTheorganiclayerisdried(sodiumsulfate)andconcentratedinvacuoTheresiduecanthenbepurifiedbyflashchromatography(SiO)ifnecessaryReferencesTetLett,,,Heterocycles,,,TMSTESTIPSTBSTBDPSBacktoCarbSynthesisTMS(trimethylsilyl)etherStandardProtectionProcedureToasolutionoftheglycosideandtriethylamine(eq)stirringinTHFat°underaninertatmosphere,isaddeddropwiseTMSCl(eq)TheresultwasallowedtowarmtoroomtemperatureandstirreduntilcompletebyTLC(usuallyh)ThesolutionisthenconcentratedinvacuoandtheresiduetakenondirectlytonextstepRemovalTheglycosideisdissolvedinTHF(~M)andTBAF(MsolutioninTHF)isaddeddropwiseat°underinertatmosphereThereactionisallowedtowarmtoroomtemperatureandstirreduntilcompletebyTLC(usuallyafewhoursifnotcompleteinthistimemoreTBAFsolutionmaybeadded)*Noteequalvolumesofglacialaceticacid(comparedtoTBAFsolution)maybeaddedtopreventremovalofacetatesorothersensitiveprotectinggroupsThereactionmixtureisconcentratedinvacuoandtheresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesJACS,,,TES(triethylsilyl)etherStandardProtectionProcedureToasolutionoftheglycosideandimidazole(eq)stirringinDMFat°underaninertatmosphere,isaddeddropwiseTESCl(eq)TheresultisallowedtowarmtoroomtemperatureandstirreduntilcompletebyTLC(usuallyovernight)AnequalvolumeofetherisaddedandthereactionmixtureisextractedthreetimeswithwaterandoncewithbrineTheorganiclayerisdried(sodiumsulfate)andconcentratedinvacuoTheproductcanthenbepurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinTHF(~M)andTBAF(MsolutioninTHF)wasaddeddropwiseat°underaninertatmosphereTheresultisallowedtowarmtoroomtemperatureandstirreduntilcompletebyTLC(usuallyafewhoursifnotcompleteinthistimemoreTBAFsolutionmaybeadded)*Noteequalvolumeofglacialaceticacid(comparedtoTBAFsolution)maybeaddedtopreventremovalofacetatesorothersensitiveprotectinggroupsThereactionmixtureisconcentratedinvacuoandtheresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesHelvChimActa,,,TIPS(triisopropylsilyl)etherStandardProtectionProcedureToasolutionoftheglycosidestirringinDMFat°underaninertatmosphere,TIPSCl(eq)andimidazole(eq)wereaddedsuccinctlyTheresultwasallowedtowarmtoroomtemperatureandstirreduntilcompletebyTLC(usuallyovernight)ThemixtureisdilutedwithequalvolumeofchloroformandextractedthreetimeswithwaterandoncewithbrineTheorganiclayerisdried(sodiumsulfate)andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinTHF(~M)andTBAF(MsolutioninTHF)wasaddeddropwiseat°underaninertatmosphereTheresultisallowedtowarmtoroomtemperatureandstirreduntilcompletebyTLC(usuallyafewhoursifnotcompleteinthistimemoreTBAFsolutionmaybeadded)*Noteequalvolumeofglacialaceticacid(comparedtoTBAFsolution)maybeaddedtopreventremovalofacetatesorothersensitiveprotectinggroupsThereactionmixtureisconcentratedinvacuoandtheresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesJOC,,,TBS(tertbutyldimethylsilyl)etherStandardProcedureToasolutionoftheglycosideinDMFat°underaninertatmosphere,TBSCl(eqforselectiveprimaryOHprotection,eqotherwise)andimidazole(toeq)wereaddedsuccinctlyTheresultwasallowedtowarmtoroomtemperatureandstirreduntilcompletebyTLC(usuallyovernight)ThemixtureisdilutedwithequalvolumeofchloroformandextractedthreetimeswithwaterandoncewithbrineTheorganiclayerisdried(sodiumsulfate)andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryORToasolutionoftheglycosideanddistilled,lutidine(eq)indryDCMunderaninertatmosphereat°,TBSOTfisaddeddropwiseoverminutesTheresultisstirreduntilcompletebyTLC(usuallyminutesifnotcompletemoreTBSOTfmaybeadded)andmethanolisaddedThemixtureisdilutedwithchloroform,washedwithwaterandbrine,driedovermagnesiumsulfateandconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalTheglycosideisdissolvedinTHF(~M)andTBAF(MsolutioninTHF)wasaddeddropwiseat°underaninertatmosphereTheresultisallowedtowarmtoroomtemperatureandstirreduntilcompletebyTLC(usuallyafewhoursifnotcompleteinthistimemoreTBAFsolutionmaybeadded)*Noteequalvolumeofglacialaceticacid(comparedtoTBAFsolution)maybeaddedtopreventremovalofacetatesorothersensitiveprotectinggroupsThereactionmixtureisconcentratedinvacuoandtheresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesJACS,,,JACS,,,JOC,,,TBDPS(tertbutyldiphenylsilyl)etherStandardProcedureTheglycosideisdissolvedinDMFatroomtemperatureunderaninertatmosphereandtreatedwithimidazole(eqperOH)followedbyTBDPSCl(eqperOH)ThereactionmixtureisstirreduntilcompletebyTLC(usuallyovernight),dilutedwithetherandwashedwithMHClfollowedbybrineTheorganiclayerisdried(magnesiumsulfate)andconcentratedinvacuoTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryRemovalToasolutionoftheglycosideinTHFatroomtemperatureinaNalgenecontainer,commerciallyavailableHFinpyridineisaddeddropwiseunderaninertatmosphereTheresultisstirreduntilcompletebyTLC(usuallyh)anddilutedwithslowadditionofsaturatedsodiumbicarbonateChloroformisaddedandthemixtureisextractedsuccessivelywithwater,saturatedcoppersulfate,andbrineTheorganiclayeristhendried(sodiumsulfate)andconcentratedTheresultingresidueispurifiedbyflashchromatography(SiO)ifnecessaryReferencesJACS,,,AlcoholprotectionMOMMEMBOMSEMDiolprotectionAcetonideBenzylidenepMethoxybenzylideneDTBS(OR)MOM(methoxymethyl)etherStandardProtectionProcedureToasolutionoftheglycosideinDCM(approxM)andHunig'sbase(N,Ndiisopropylethyla

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羟基、氨基及氨基酸的各种保护基及去保护方法大全

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