Lecture 7.1 Rxns of hydroxygroups-2
Lecture'7.1'Rxns'of'hydroxyl' groups72
1.Cyclic acetal formation:5-ring vs 6-ringOHOHHO(CH2)(CH2)Sn1processCH2)OHR-+ H20(CH2)nRcyclic acetal
1.#Cyclic#acetal#forma0on:#54ring#vs#64ring#
MeOH+HOOHMeHO（HMe)Me(H+OOHMeOMeHOH+HOOHHOPhHHOHPh
2.Acetonide protection of carbohydrate hydroxyl groupsHOHOHHMeo)+oMetOMeMeO4HOOMeOMeMeoOMeHOHOOH'OHHOH+OH
2.#Acetonide#protec0on#of#carbohydrate#hydroxyl#groups#
2.1 Rxn of glucose with acetone and acidHOOHH+H+HOHOOH0HO''OHHOHOOHOHgluofuranoseglucopyranosediacetoneglucose
2.1#Rxn#of#glucose#with#acetone#and#acid#
2.2 Rxn of galactose with acetoneandacidOHHCH+HOHO'OHOHdiacetonegalactosegalactopyranose
2.2#Rxn#of#galactose#with#acetone#and#acid#
2.3Rxnofmannosewithacetoneand acidHOOhH+H+HOHOIOH?HOOHOHHOOHOHmannopyranosemannofuranosediacetonemannose
2.3#Rxn#of#mannose#with#acetone#and#acid#
3.BenzylideneprotectionofcarbohydratehydroxylgroupsHOHMeOOMePh0PhH福OHOH+OHOHOMeOMePhHOH.OHCMeOOMeHPhHOHOH+OHOHOMeOMe
3.#Benzylidene#protec0on#of#carbohydrate#hydroxyl#groups#
4.Butane diacetal protection of diolsHOHOMeOHOMeOHOHOMe0MeoH+OOMeSMeSMeOHOMeOH0OMeSMe
4.#Butane#diacetal#protec0on#of#diols
5.Cyclicacetalhydrolysis:deprotectionofcarbohydratehydroxylgroupsHOAcOHHO"H20HOHO
5.#Cyclic#acetal#hydrolysis:#deprotec0on#of#carbohydrate## hydroxyl#groups#