Studies of aminosugars. XX. The synthesis of 6-O-(3-amino-3-deoxy-alpha-D-glucopyranosyl)-2-deoxystreptamine.

6-O-(3-Amino-3-deoxy-α-D-glucopyranosyl)-2-deoxystreptamine (3AD) which is a glycoside component of kanamycin A has been synthesized. Amino and hydroxyl groups of 2-deoxystreptamine were masked with carbobenzoxy and isopropylidene groups to give racemic mono-O-isopropylidene-di-N,N′-carbobenzoxy-2-deoxystreptamine with which 3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-D-glucopyranosyl chloride was condensed by a modified Koenigs-Knorr reaction. Removal of all the masking groups followed by N-dinitrophenylation, acetylation and chromatography gave the product identical with an authentic specimen of the penta-O-acetyl-tri-N-(2,4-dinitrophenyl) derivative of the natural 3AD. The synthetic product was further led to 3AD identical with a natural sample.

[1]  T. Tsumura,et al.  Studies of aminosugars. XIX. Synthesis of O-benzyl-alpha-halogeno derivatives of 3-acetamido-3-deoxy- and 6-acetamido-6-deoxy-D-glucose. , 1968, Bulletin of the Chemical Society of Japan.

[2]  K. Tatsuta,et al.  THE TOTAL SYNTHESIS OF KANAMYGIN A , 1968 .

[3]  K. Tatsuta,et al.  Synthesis of neamine. , 1980, The Journal of antibiotics.

[4]  K. Tatsuta,et al.  Synthesis of trehalosamine. , 1967, The Journal of antibiotics.

[5]  K. Tatsuta,et al.  Studies of antibiotics and related substances. XXXII. Syntheses of neamine and its analogue. , 1967, Bulletin of the Chemical Society of Japan.

[6]  K. Tatsuta,et al.  Studies of Aminosugars. XIV. Syntheses of 6,6′-Diamino-6,6′-dideoxymaltosylamine, 1′,6,6′-Triamino-,1′,6,6′-trideoxysucrose and 6,6′-Diamino-6,6′-dideoxytrehalose , 1967 .

[7]  S. Koto,et al.  Studies of Aminosugars. XIII. The Synthesis of Paromamine , 1966 .

[8]  S. Umezawa,et al.  Structure of (2-amino-2-deoxy-alpha-D-glucosyl)-deoxystreptamine produced by acid reversion. , 1966, The Journal of antibiotics.

[9]  K. Tatsuta,et al.  Studies of Aminosugars. XII. The Absolute Structure of Kanamycin as Determined by a Copper Complex Method , 1966 .

[10]  K. Tatsuta,et al.  Studies of Aminosugars. XI. Configurational Studies of Aminosugar Glycosides and Aminocyclitols by a Copper Complex Method , 1966 .

[11]  H. Umezawa,et al.  Structure studies on kanamycin. , 1958, The Journal of antibiotics.

[12]  K. Nitta,et al.  Production and isolation of a new antibiotic: kanamycin. , 1957, The Journal of antibiotics.