Facile synthesis of 6-amino-6-deoxycellulose

Synthesis of regioselectively brominated cellulose esters and 6-cyano-6-deoxycellulose esters

“…In each case, the DS of the bromide was determined to be near 1.0. In their original paper, Furuhata et al determined that the DS of their nonesterified product was 0.91 (Furuhata et al 1992), and the highest DS obtained using this reaction and reported in the literature was 0.98 (Matsui et al 2005). Ours is the first literature report of a DS of greater than 1.0 from this reaction.…”

“…However, there are relatively few reports over the past two decades of derivatives being synthesized from the brominated cellulose, especially when compared to the level of interest shown for derivatives synthesized from similar but less regiospecifically substituted tosyl cellulose intermediates (Fox et al 2011). One possible reason for this relative lack of attention is the fact that 6-bromo-6-deoxycellulose is poorly soluble in common organic or aqueous solvents, thus limiting high conversion in further synthetic steps to those that lead to reactive dissolution (Saad et al 1996;Aoki et al 1999;Matsui et al 2005) or in which the starting material is re-dissolved in DMAc/LiBr (Furuhata and Ikeda 1999;Aoki et al 1996). That problem was overcome in this study by the in situ esterification of the remaining free hydroxyl groups on 6-bromo-6-deoxycellulose.…”

Synthesis of 6-deoxy-6-chloro and 6-deoxy-6-bromo derivatives of scleroglucan as intermediates for conjugation with methotrexate and other carboxylate containing compounds

“…This reagent has been successfully used for the chlorination of primary hydroxyl groups of polysaccharides such as amylose (Cimecioglu, Ball, Kaplan, & Huang, 1994), pullulan (Mocanu, Constantin, & Carpov, 1996), laminaran (Khan, Bosco, Konowicz, Stucchi, & Rizzo, 1996) and cellulose (Ishii, Ishizu, & Nakano, 1977;Matsui, Ishikawa, Kamitakahara, Takano, & Nakatsubo, 2005). An attempt to rationalize the reaction of this combination of reagents with alcohols was made (Cimecioglu et al, 1994;McCormick, Dawsey, & Newman, 1990).…”

A Novel Cellulose-Based Azide Energetic Material: 1-Azido-2-hydroxypropyl Cellulose Ether

“…As early as 1989, Gilbert published a preparation of an azidodeoxycellulosebased high energy binder used in solid propellants, wherein nitrocellulose was used as the starting reactant, which was transferred into an iodine cellulose intermediate and subsequently subjected to sodium azide, to obtain the azidodeoxycellulose [5,6]. In addition, it was disclosed in another report that azidodeoxycellulose can be obtained by reacting cellulose tosylate with sodium azide [7][8][9][10][11]. In the above-mentioned studies, there are considerable defects that have adversely affected the application of the products as energetic materials: (1) simply, the azido group is introduced into the main chain of cellulose, whereas the semi-rigid conformation of the cellulose chain remains; (2) a certain number of the hydroxyl groups are consumed, and the activity of a further modification by nitrification is significantly reduced; (3) most important, the iodine or the p-tosyl group in the final products thereof is difficult to be removed completely.…”