Synthesis of carbohydrate molecules that contain peptide bond

In this study, 1,2-O-(R)-trichloroethlydene-α-D-glucufuranose (α-chloralose), 1,2-O-(S)-trichloroethlydene-β-D-glucufuranose (β-chloralose) and D-arabinose were used as a starting sugars.The aim of this work is the synthesis of carbohdrate molecules on which carrying peptide bond fromthe reaction of carboxylic acids with amine derivatives.Firstly, D-arabinose was converted to 1,2-O-trichloroethlylidene-α-D-arabinofuranosederivative with chloral hydrate. Than, this molecule was converted to tosyl derivative with TsCl. Later,this formation was converted to azide form with NaN3. Obtained azide formation was reacted withvarious reducing agent in order to get the related aminosugar derivatives. But, pozitive results couldnot be obtained.As a second way, the reduction of N-oxime derivatives were experimented to get the aminosugar formation. 1,2-O-trichloroethlylidene-α-D-arabinofuranose was converted to pentadialdose formwith NaIO4, later this pentadialdose derivatives converted to an oxime formation with NH2OH.HCl.Obtained oxime derivative was reacted with Zn dust in order to get the related aminosugar derivatives.But, the positive results also could not be obtained.Same reaction was done for 3-O-methly-1,2-O-trichloroethyldene-α-D-glucofuranose. Thegood results could not be obtained again.As an other way, it was prefered that uronic acid formation of α-chloralose and 3-O-methly-1,2-O-trichloroethyldene-α-D-glucofuranose (known as a carboxyclic acid derivatives of sugars ) wereused for amide synthesis. For this steps, firstly α-chloralose and 3-O-methly-1,2-O-trichloroethyldene-α-D-glucofuranose reacted with NaIO4 in order to get the related pentadialdose forms respectively.Later, this pentadialdose derivatives reacted with conc.HNO3 to obtain related uronic acids derivatives.It was tested that these uronic derivatives had been reacted with a benzyl amine presence ofDCCI that serve as a coupling reagent.Key Words: Coupling Reagents, DCCI, Synthesis of Amides, Reduction Of Oximes, Uronic Acids,Reduction with Zn.