2-Amino-2-deoxy-o-D-glucopyranosyl

Chemical Name 0-2,6-diamino-2,6-dideoxy-(3-L-idopyranosyl-(1- -3)-0-(3-D-ribofuranosyl-(1- -5)-0-[2-amino-2-deoxy-o -D-glucopyranosyl-(1- -4)I -2-deoxystreptamine... 

Coupling of 237 with the protected 2-amino-2-deoxy-o -D-glucopyranosyl bromide (348) in dichloromethane in the presence of silver triflate afforded a diastereoisomeric mixture. The isomer related to the natural one was depro-tected with sodium in liquid ammonia, to give the carba-trehalosamine... 

Paromamine, neamine, 4-0-(6-amino-6-deoxy- -D-glucopyranosyI)-2-deoxystreptamine, 5-0- (2-amino-2-deoxy-o-D-glucopyranosyl) -2-deoxy-streptamine, kasugamycin, and a,a-trehalosamine have been synthesized. A common feature in the structures of these antibiotics is the presence of an a-o-glycosidic linkage. In the total syntheses, modified Koenigs-Knorr reactions, or addition of nitrosyl chloride " to an enose, were successfully used. 

An improved synthesis of paromamine was effected with a Schiff base and a more protected 2-deoxystreptamine. The cyclohexylidene derivative of l,3-di-2V-(ethoxycarbonyl)-2-deoxystreptamine (79, race-mate) was condensed with 3,4,6-tri-0-acetyl-2-deoxy-2-(p-methoxy-benzylideneamino)-a-D-glucopyranosyl bromide (see Refs. 174 and 175 on p. 153) to give two products (80 and 81), which, after removal of the protecting groups, furnished paromamine (78) and an isomer, 6-0-(2-amino-2-deoxy-o-D-glucopyranosyl)-2-deoxystreptamine (82). The latter was devoid of antibacterial activity. 

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