The present study reports the first time and novel synthetic methodology for halogenation & C-N bond formation reactions in the backbone of D-Glucose. The key steps include chlorination and amination of glucose. The synthesized products are designated as Glucose chloride & Synthesized Chitosan respectively. Synthesized Chitosan resembles with the unit structure of Chitosan i.e. Oligomeric Chitosan and it is water soluble. FTIR spectrum of D-Glucose the characteristic broad peak at 3350cm-1 for stretching of hydroxyl (–OH–) group has disappeared in halogenation reaction showing the substitution of chloride & having characteristic sharp peak at 3150cm-1 for stretching of Amine (–NH2–) group indicating replacement of chloride group with amine. The synthesis was completely characterized by FT-IR, C H N S analysis, 1H NMR, 13C NMR, DEPT 135 NMR, XRD and GC-MS.