Ram Babu - Academia.edu (original) (raw)

Papers by Ram Babu

Research paper thumbnail of 3,3-Diphenyl-2-Morpholinone Derivatives Of 2-Amino-2-Deoxy-D-Allose

2-Amino-2 Deo:'y-D-Al'losc. Abstract r.:of Dissertation A new cycli. c protcctbre qrcu':'l has hc... more 2-Amino-2 Deo:'y-D-Al'losc. Abstract r.:of Dissertation A new cycli. c protcctbre qrcu':'l has hccn fu-5(;d to the cis amino alc(.:hol aroup oi bf:!nzy'i 2-ai't::.~o'-4, 6-'c~b~nzyiidt2n<:?-2-deoxY~ ""i'>-:-Allopyr.a!'lOSide, by wv.y of a u;tiqu,~ r~ ,a:r~anqemcn ts mcicha:liSin•-To ~si:a~Jlisl~ the 2-morpholinor.e StJ:'Uyt1Jre, Ci:tef!liC:al St~d. .i }~S, Sl.&•-:h as redt.tC~i.on etnd acetyl atiori, were conducted. Comparative s-pectrol';ccpi~ studi~s usino ir, pmr 3nd c-13 nmr COr.firtr.ed th. e a!;,Sil'1ned structures. The 2-mo:i•pho~inone xl.n<r wa~ cleaved by mild alkalint: hydrolysis and caul d be •":: losed •a.na.ir. with acetic ~nhy~ldde ,in pyridine. An cx~zoi::.dinonti der i'i at.i,.re o~ bcn~yl 2amino-4 ~ 6-o-benzylirl~nc-2-::lecxy"'i'•-D-allcn.ry.;::-,:.,s.idc was preparC'd: in quantl.ta":..ivg y.i.el<.Cby a m.od :i i!icatio:l of a kno\-tn tri~t~~od. • Protective q.r.oup ?rot;>er~i s s c•~ : th~ O)l: i'l~oli{lincnt! w~ra st.:udied prior to th~ ex;:,~. ination o f th~ 2-::t6rt:iholinone cyclic prot~ctivc ~rcuf>. rho s.,:lccti•-•~ n •mov.:tl of the benzyl aCTiycon was achi{!vcd i.n excoller..t y.k ~<'f hy ~atalytic hy1lroganatio~, for {loth .,..orp~.olir.;.,r~<~ .,nd OY.<\ZOlidinonc protected ocn?.y~.fr'iJ-<t 1-lopyranc.>sidt!:O • 'The seledtivc removal of the 4 ,6-:-o,-bcriz~;l idcnc (fCO'Jfin presence of a 2-mo r'Dholinor.o:: rin<t was po~sibli:! iri h.i.gh yield. The clea v;t.qe of the 2-'morp:"iolinnn•J pro,• tective qro1.1p was accompUshcd in two. fi..teps~ ~ild alkaline • hydrolysis clc,:,yed Lhe e s ter functio!l of the rinq .and mild <lCidic hyurolJsis cleav~rl its ar:oi::le function. .. INTRODUC?!Oi l Am:tnosugars play diversified and important roles iti biochcffii::;tcy, as building blocks of homoand heteropolynk'?rs arid of con;>le;< molecules~ such as microbial polysaccharides, :glycoproteins, gungliosides ~ en~~nrs, glycolipids, antibiotics and nucleosidcs. 1 The structure of amino-sUgars, which shows features of' both amino acids and cor.rnon su~;ars, gives them unique lyophilicity, that deroonstrat~s their presence in. 100st prote.ins and many lipids. 2 Their presence as coMponents of high molecular weight conpounds, in the surface of eells, or in the intercellular matrix, suggests participation in rrecha~sr..z t~r 'lihich c~Us recognize other cells and large molecules. 'I'hese nr:dno sugar: :

Research paper thumbnail of 3,3-Diphenyl-2-Morpholinone Derivatives Of 2-Amino-2-Deoxy-D-Allose

2-Amino-2 Deo:'y-D-Al'losc. Abstract r.:of Dissertation A new cycli. c protcctbre qrcu':'l has hc... more 2-Amino-2 Deo:'y-D-Al'losc. Abstract r.:of Dissertation A new cycli. c protcctbre qrcu':'l has hccn fu-5(;d to the cis amino alc(.:hol aroup oi bf:!nzy'i 2-ai't::.~o'-4, 6-'c~b~nzyiidt2n<:?-2-deoxY~ ""i'>-:-Allopyr.a!'lOSide, by wv.y of a u;tiqu,~ r~ ,a:r~anqemcn ts mcicha:liSin•-To ~si:a~Jlisl~ the 2-morpholinor.e StJ:'Uyt1Jre, Ci:tef!liC:al St~d. .i }~S, Sl.&•-:h as redt.tC~i.on etnd acetyl atiori, were conducted. Comparative s-pectrol';ccpi~ studi~s usino ir, pmr 3nd c-13 nmr COr.firtr.ed th. e a!;,Sil'1ned structures. The 2-mo:i•pho~inone xl.n<r wa~ cleaved by mild alkalint: hydrolysis and caul d be •":: losed •a.na.ir. with acetic ~nhy~ldde ,in pyridine. An cx~zoi::.dinonti der i'i at.i,.re o~ bcn~yl 2amino-4 ~ 6-o-benzylirl~nc-2-::lecxy"'i'•-D-allcn.ry.;::-,:.,s.idc was preparC'd: in quantl.ta":..ivg y.i.el<.Cby a m.od :i i!icatio:l of a kno\-tn tri~t~~od. • Protective q.r.oup ?rot;>er~i s s c•~ : th~ O)l: i'l~oli{lincnt! w~ra st.:udied prior to th~ ex;:,~. ination o f th~ 2-::t6rt:iholinone cyclic prot~ctivc ~rcuf>. rho s.,:lccti•-•~ n •mov.:tl of the benzyl aCTiycon was achi{!vcd i.n excoller..t y.k ~<'f hy ~atalytic hy1lroganatio~, for {loth .,..orp~.olir.;.,r~<~ .,nd OY.<\ZOlidinonc protected ocn?.y~.fr'iJ-<t 1-lopyranc.>sidt!:O • 'The seledtivc removal of the 4 ,6-:-o,-bcriz~;l idcnc (fCO'Jfin presence of a 2-mo r'Dholinor.o:: rin<t was po~sibli:! iri h.i.gh yield. The clea v;t.qe of the 2-'morp:"iolinnn•J pro,• tective qro1.1p was accompUshcd in two. fi..teps~ ~ild alkaline • hydrolysis clc,:,yed Lhe e s ter functio!l of the rinq .and mild <lCidic hyurolJsis cleav~rl its ar:oi::le function. .. INTRODUC?!Oi l Am:tnosugars play diversified and important roles iti biochcffii::;tcy, as building blocks of homoand heteropolynk'?rs arid of con;>le;< molecules~ such as microbial polysaccharides, :glycoproteins, gungliosides ~ en~~nrs, glycolipids, antibiotics and nucleosidcs. 1 The structure of amino-sUgars, which shows features of' both amino acids and cor.rnon su~;ars, gives them unique lyophilicity, that deroonstrat~s their presence in. 100st prote.ins and many lipids. 2 Their presence as coMponents of high molecular weight conpounds, in the surface of eells, or in the intercellular matrix, suggests participation in rrecha~sr..z t~r 'lihich c~Us recognize other cells and large molecules. 'I'hese nr:dno sugar: :