Glucosamine 6-deoxy-3-0-methyl

N-methyl-L-glucosamine (N methyl-2-amino-2-deoxy-L-glucopyranose). 

O-Methyl-D-glucosamine Hydrochloride (2-Amino-2-deoxy-6-0-methyl-... 

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... 

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. 

The synthesis of this substance, starting with methyl 2-acetamido-4,6-0-benzylidene-2-deoxy-a-D-glucoside, was performed as follows. The two isomers which were formed were separated on a Dowex 50 colunm, and one (Md +109°) was shown to be identical with natural muramic acid. The strong dextrorotation effectively ruled out the L-glucosamine configuration, and the configuration of the lactic moiety was deduced to be most likely d. The second isomer had [ ] +52° and differed, in its behavior on resin columns and in paper chromatography, from natural muramic acid. 

Most imidazoline, imidazolone, and imidazole derivatives are stable ring structures and usually exist only in the cyclic forms. For example, in the reaction of methyl 2-deoxy-2-isothiocyanato-a-D-glucopyranoside 149 with D-glucosamine 148, a-deoxy-2-(3-substituted thioureido)-D-aldose, 150, is presumably the reaction intermediate. However, the ring-chain tautomeric equilibrium of 150 shifts towards the cyclic form to yield 151 which is the only detectable form by NMR analysis (Scheme 41) <1999TA3011>. 

Very recently, amino deoxyglucmonic acids were used in the construction of disaccharide libraries [45]. In the report, methyl 3-azido-3-deoxy-4-0-methyl-j8-D-glucmonic acid was prepared and glycosidically linked to a protected glucosamine, yielding a disaccharide with both amino and carboxamide fimctionalities. The azide was subsequently reduced and reacted with several isocyanates, providing libraries of j8-linked disaccharides (Fig. 24). 

During the elucidation of the structure of mannosidostreptomycin by methylation. Fried and Stavely isolated two derivatives of a dimethyl ether of iV-methyl-L-glucosamine. In order to compare their physical constants with those of a known compound in the n-series. Fried and Walz prepared derivatives of 2-deoxy-3,6-di-0-methyl-2-methylamino-n-glucose. The addition of methylamine and hydrogen cyanide to 2,5-di-0-methyl-D-arabinose (prepared by the periodate oxidation of 3,6-di-O-methyl-D-glucose) was followed by hydrolysis, and jdelded a mixture of a dextro- and a levo-rotatory acid. The dextrorotatory product was con-... 

The first preparation of a 4,6-dimethyl ether of 2-amino-2-deoxy-D-glucose was reported by Haworth, Lake, and Peat. Action of ammonia on methyl 2,3-anhydro-4,6-di-0-methyl-j3-D-mannoside, followed by N-acetylation of the product, led to the formation of methyl 3-acetamido-3-deoxy-4,6-di-0-methyl- S-D-altroside (in high yield) and of methyl 2-acetamido-2-deoxy-4,6-di-0-methyl- S-D-glucoside (in a 9.4% yield). Methylation of the latter compound yielded a 3,4,6-trimethyl ether identical with the one prepared from natural n-glucosamine. ... 

Synthesis of the 3,4,6-trimethyl ether of 2-deoxy-2-methylamino-n-gluconic acid was carried out along lines similar to those of the synthesis of the 3,6-dimethyl ether. By the addition of methylamine and hydrogen cyanide to 2,3,5-tri-O-methyl-n-arabinose, followed by hydrolysis, only one compound was formed, and this was related to n-glucosamine on the basis of its optical rotation. An attempt to obtain the aldose derivative by reduction with sodium amalgam was not successful, probably because of the impossibility of 5-lactone formation. 

S.3.3.2 Synthesis from o-glucosamine Allosamizoline (8) has also been synthesized from D-glucosamine (Scheme 3). Methyl 2-amino-4,6-0-benzylidene-3-0-benzyl-2-deoxy-a-D-glucopyranoside" (26), obtained from D-glucosamine hydrochloride (25), was converted into the corresponding M,A -dimethylurea derivative, which underwent hydrolysis with aqueous acetic acid to give the diol 27 (91%). Selective iodination of the primary position and subsequent protection of the secondary hydroxyl group with... 

Methylamino)-2-deoxy-a-7-glucopyranose A/-Methyl-a-7-glucosamine CgHggNOg 42862-96-9 193.198 glass sMeOH... 

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