20744-51-8

Basic information

• Product Name: TOBRAMYCIN A
• Synonyms: Kanamycin A Related Compound 2;6-O-(3-AMINO-3-DEOXY-ALPHA-D-DEOXYGLUCOPYRANOSYL)-2-DEOXY-STREPTAMINE;TOBRAMYCIN A;6-o-(3-amino-3-deoxy-alpha-d-glucopyranosyl)-2-deoxy-d-streptamin;antibioticnk1012-2;6-O-(3-AMINO-3-DEOXY-ALPHA-D-DEOXYGLUCOPYRANOSYL)-2-DEOXY-STREPAMINE;6-O-(3-Amino-3-deoxy-α-D-glucopyranosyl)-2-deoxy-D-streptamine;NK-1012-2
• CAS NO: 20744-51-8
• Molecular Formula: C₁₂H₂₅N₃O₇
• Molecular Weight: 323.34
• EINECS: 203-170-6
• Product Categories: Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Carbohydrates & Derivatives, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 20744-51-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 613.3°Cat760mmHg
• Flash Point: 324.7°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 1.32E-17mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Heated, Sonicated)
• PKA: 13.07±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: TOBRAMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: TOBRAMYCIN A(20744-51-8)
• EPA Substance Registry System: TOBRAMYCIN A(20744-51-8)

Safety Data

• Hazardous Substances Data: 20744-51-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Brown Solid

Uses

Different sources of media describe the Uses of 20744-51-8 differently. You can refer to the following data:
1. An impurity of Tobramycin (T524000(P)), which is a single factor antibiotic comprising about 10% of nebramycin, the aminoglycosidic antibiotic complex produced by Streptomyces tenebrarius; antibacterial.
2. An impurity of Tobramycin (T524000).

InChI:InChI=1/C12H25N3O7/c13-3-1-4(14)11(10(20)7(3)17)22-12-9(19)6(15)8(18)5(2-16)21-12/h3-12,16-20H,1-2,13-15H2/t3-,4+,5+,6-,7+,8+,9+,10-,11-,12+/m0/s1

Upstream product

• 179533-32-5 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 
• 1147358-80-2 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A 
• 1037515-73-3 1,3,6',3”-tetra-azido-kanamycin A 
• 59-01-8 kanamycin A 
• 3847-27-6 Kanamycin A sulfate 
• 144218-66-6 2''-O-acetyl-6'-N-(benzyloxycarbonyl)-4'-O-(benzylsulfonyl)-1,3,3''-tri-N-tosylkanamycin A 
• 179533-31-4 1,3,6',3''-tetra-N-tosylkanamycin A 
• 179533-33-6 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 
• 133-92-6 kanamycin A sulfate 
• 103358-05-0 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine 
• 144218-74-6 6-O-(4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 
• 179533-34-7 4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-6-O-(4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 

Downstream Products

• 22860-83-9 (1S)-N,N'-diacetyl-O⁴-(3-acetylamino-3-deoxy-α-D-glucopyranosyl)-2-deoxy-streptamine 

Relevant articles and documents

Synthesis of ring II/III fragment of Kanamycin: A new minimum structural motif for aminoglycoside recognition

A novel protocol has been established to prepare the kanamycin ring II/III fragment, which has been validated as a minimum structural motif for the development of new aminoglycosides on the basis of its bactericidal activity even against resistant strains. Furthermore, its ability to act as a AAC-(6′) and APH-(3′) binder, and as a poor substrate for the ravenous ANT-(4′), makes it an excellent candidate for the design of inhibitors of these aminoglycoside modifying enzymes.

Synthesis of 4'-deoxy-4'-fluorokanamycin A and B

4'-Deoxy-4'-fluorokanamycins A (17) and B (25) have been prepared through fluorinating ring-opening of the D-galacto-3',4'-oxiranes (8 and 21) derived from kanamycin A and B with potassium hydrogenfluoride in ethane-1,2-diol.The mechanism of preponderant formation of the 4'-deoxy-4'-fluoro-D-gluco ( 9 and 22) over the 3'-deoxy-3'-fluoro-D-gulo derivatives was discussed.In the synthesis of 25, the unusual 3',6'-epimine (23) was the main product along with the 4'-deoxy-4'-fluoro derivative.The mechanism of this reaction is also discussed.Both 17 and 25 were active against resistant bacteria producing aminoglycoside-adenylylating enzymes for HO-4'.

Chemistry of kanamycin. V. The structure of kanamycin.

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