Streptamine 6-0- -2-deoxy-, preparation

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. ... 

Variously derivatized 2-deoxy- and 2,5-dideoxy-streptamines have been synthesized 2,5-dideoxystreptamine was prepared from kanamycin by a simple procedure, and 5 0-(2,3-dideoxy-a-D-e 7r/iro-hexopyranosyl)-2-deoxy-strepta-mine dihydrochloride was obtained by glycosidation of a 2-deoxystreptamine derivative with tri-O-acetyl-D-glucal and hydrogenation. " The preparation of a 5-aminocyclohexanetetrol from kanamycin A is mentioned in Chapter 18. 

Numerous reports describe the modification of natural amino-glycoside antibiotics or products derived from them by conventional methods. 1-/ -Alkylated kanamycins can be prepared very efficiently by utilizing an O N acyl migration to protect the sugar amino-groups selectively, leaving the deoxy-streptamine amino-groups free-, a formylation-deformylation sequence then... 

There have been many syntheses reported this year in quest of compounds with improved biological activity. Syntheses which involve glycosylation of streptamine derivatives have included the preparation of 4-0-(2-amino-2-deoxy-a-D-glucopyranosyl)- and 4-0-(6-amino-6-deoxy-a-D-glucopyranosyl)-2,5-dideoxystreptamine, the latter showing remarkable antimicrobial activity, ... 

Pure, crystalline gentamycin A has been prepared and was shown to possess structure V in which the known paromamine ( pseudoneamine) is connected through Ce of the 2-deoxy-streptamine moiety to of a novel 3-methylamino-3-deoxy-... 

Deoxy-3-fluoro-D-glucose has been used to prepare 4-amino-3-fluoro-2-hydroxybutanoic acid derivatives which were coupled to kanamycin A and B via amide links to N-1 of the streptamine unit. ... 

Purified transamidinase preparations from S. griseus and 5. hikiniensis and a crude preparation from S. hluensis catalyzed, when incubated in the presence of L-arginine, the formation of phosphate esters of N-amidino-scyZ/o-inosamine, N-amidino-streptamine and N-amidino-2-deoxy-streptamine from phosphate esters of scy/Zo-inosamine, streptamine and 2-deoxy-streptamine, respectively. None of the enzyme preparations, however, catalyzed the addition of a second amidine group to these monoguanidinated molecules. It is not known whether this second guanidine group is derived via another transamidination reaction or by a different mechanism. 

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