2,3-Diamino-2,3-dideoxy-α-d-glucose

Publisher Summary This chapter discusses the synthesis of 2,3-diamino-2,3-dideoxy- d -glucose, which was first synthesized by double inversion at C-3 in methyl 2-benzamido-4,6-O-benzylidene-2-deoxy-β- d -glucopyranoside. A second approach to this sugar utilized the nitromethane synthesis. Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α- d -glucopyranoside is dissolved in 150 ml of pyridine, and 12 ml of methanesulfonyl chloride is added with cooling to 0°. The mixture is stored at 0° for 16 hours and poured into ice and water. While in benzyl 2,3-diacetamido-2,3-dideoxy-α- d -glucopyranoside, a solution of 5.0 g of V in 250 ml of 80% acetic acid is heated at 90° for 45 min. The solution is evaporated under diminished pressure, and acetic acid is removed by codistillation with water. The crystalline residue is dissolved in 200 ml of methanol and hydrogenated for 1.5 hours after addition of 1 g of 10% palladium on carbon in a stream of hydrogen.