3 -Methylamino-3 -deoxy

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-... 

Reaction of 1,3-propanediamine and a mixture of a and isomers of 5-bromo-5-deoxy-D-xylofuranose in H2O for 10 min gave 1 R-(la,8p,9a9aa)-7,8,9-trihydroxyperhydropyrido[l, 2-u]pyrimidine (112, R = H) in 27% yield (99T6759). Reaction of 5-bromo-5-deoxy-D-xylofuranose and A -methyl-1,3-propanediamine in H2O at room temperature afforded a 5 1 mixture of 1-methyl 117 and 5-methyl 118 derivatives of 7,8,9-trihydroxyperhydropyr-ido[l, 2-u]pyrimidine 112 (R = H). When this reaction was carried out in the presence of 3 moles of NEts the product ratio of 117 to 118 was 1 2. The influence of NEt3 on the product ratio may be a consequence of it scavenging HBr and freeing the more basic and more nucleophilic methylamino group for participation in the displacement reaction. 

Chemical Name 0-2-Deoxy-2-(methylamino)-a-L-glucopyranosyl-(1 2)-0-5-deoxy-3-C-(hydroxymethyl)-a-L-lyxofuranosyl-(1 4)-N,N -bis(aminoiminomethyl)-D-streptamine... 

Chemical Name 0-2-amino-2,3/4.6-tetradeoxy-6-(methylamlno)-a-D-erythrohexopyranosyl-(1->-4)-0-(3-deoxy-4-C-methyl-3-(methylamino)-/3-L-arabinopyranosyl-(1->-6)-2-deoxy-D-streptamine... 

Such names as bacillosamine for 2,4-diamino-2,4,6-trideoxy-D-glucose and garosamine for 3-deoxy-4-C-methyl-3-methylamino-L-arabinose are not recommended, as they imply replacement of OH by NH2 in a nonexistent parent sugar. 

Note. The alternative name using a substituent prefix (see 2-Carb-35.1) is 3,4,6-tri-0-acetyl-2-amino-2-deoxy-l-0,2-N-[(methylamino)methylylidene]-a-D-glucopyranose. 

CN 4-pyridinecarboxylic acid hydrazide, hydrazone with 0-2-deoxy-2-(methylamino)-a-L-glucopyranosyl-... 

The reaction of 2-deoxy-3,4,6-tri-0-methyl-2-methylamino-D-glucopyranose 149 with methyl(phenyl)phosphonic dichlorides (106a-b) or methylthiophosphonic dichloride in benzene in the presence of triethylamine afforded mixtures of four isomers of the corresponding 1,3,2 oxazaphospholidine-2-ones 150, 151 and... 

Deoxy-2-methylamino-L-glucose (N-methyl-i.-glucosamine) NHCH, HO HO H HOH2 C—C—C—C—C—CHO H H HO H the antibiotic streptomycin... 

A methylation analysis of S14, performed in the authors laboratory,44 gave 2,3,4,6-tetra-O-methyl-D-galactose, 2,4,6-tri-O-methyl-D-galactose, and 2,3,6-tri-O-methyl-D-glucose in the proportions 1 1 1. Although these are the same components as previously reported, the proportions are different. In addition to these sugars, 2-deoxy-3-0-methyl-2-(methylamino)-D-glucose was also obtained. 

IV- methy 1-L- gluco s amine (2-deoxy-2-methylamino-L-glucose)... 

The other component parts of streptomycin, namely L-streptose and the aminosugar 2-deoxy-2-methylamino-L-glucose (A -methyl-L-glucosamine), are also ultimately derived from o-glucose. Gentamicin Ci contains two aminosugars, L-garosamine and D-purpurosamine. 

Streptomycin Streptomycin, fran5-2,4-diguanidino-3,5,6-trihydroxycyclohexyl-5-deoxy-2-0-(2-deoxy-2-methylamino-a-L-glucopyranosyl)-3-C-hydroxymethyl- 8-L-lyxo-pentofura-noside (32.4.1), is isolated from a culture liquid of the vital activity of the actinomycete S. griseus [238-247]. 

Methylamino-CD (MeNH) 6A,6D-dimethylamino-/3-CD Heptamethylamino-/3-CD (39) 6-Trimethylammonio-deoxy-CD (TMA) 6[(3-Aminoethyl)amino]-6-deoxy-CD (AEA)... 

In an attempt to elaborate50 a synthetic access to DL-garosamine [126, 3-deoxy-4-C-methyl-3-(methylamino)-DL-arabinopyranose], the 1,5-lactone of 5-hydroxy-4-methyl-3-pentenoic acid (124) was oxy-aminated, to yield 2,3-dideoxy -C-methyl-3-p-toluenesulfonamido-DL-enyfhro-pentono-l,5-lactone (125). Introduction of a hydroxyl... 

C-Methyl-D-glucuronic acid (20) 3-Deoxy-4-C-methyl-3-(methylamino)-L-arabinose (21)... 

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