Streptamine 6-0- -2-deoxy-> synthesis

Another synthesis of 95 (and 97) reported by Umezawa and co-workers involved the condensation of 6-azido-2,3,4-tri-0-benzyl-6-deoxy-a-D-glucopyranosyl chloride (98) with the protected 2-deoxy-streptamine 99. The 4- (100) and 6-glycoside (101) were obtained, and from these were prepared 95 and 97, respectively. 

A synthesis of hexa-acetyl streptamine (14) from 2-acetamido-2-deoxy-D-glucose is outlined in Scheme 5. The tritium-labelled 2,6-dideoxystreptamine (15) has been prepared from a trihydroxycyclohexanone derivative by a sequence of standard reactions that included the reduction of the ketone group with sodium borotritide. ... 

Umezawa s group has reported the synthesis of 4 -deoxy-kanamycin via the coupling of an appropriately derivatized 6-amino-4,6-dideoxy-D-x j /n-hexosyI chloride with a streptamine derivative. The enzymic phosphorylation and antibacterial activity of the modified antibiotic were examined. Ribostamycin has been converted into butirosin B and its 3, 4 -dideoxy derivative, thus formally... 

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