236401-43-7

Basic information

• Product Name: TOBRAMYCIN A
• Synonyms: D-Streptamine, 4-O-(3-amino-3-deoxy-α-D-glucopyranosyl)-2-deoxy- (9CI)
• CAS NO: 236401-43-7
• Molecular Formula: C12H25 N3 O7
• Molecular Weight: 323.34
• Mol File: 236401-43-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: TOBRAMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: TOBRAMYCIN A(236401-43-7)
• EPA Substance Registry System: TOBRAMYCIN A(236401-43-7)

Safety Data

• Hazardous Substances Data: 236401-43-7(Hazardous Substances Data)

Upstream product

• 144218-67-7 3',4'-anhydro-6'-N-(benzyloxycarbonyl)-4'-epi-1,3,3''-tri-N-tosylkanamycin A 
• 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 
• 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 
• 2037-48-1 2-deoxystreptamine 
• 185114-94-7 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose 
• 205676-46-6 phenyl 3-azido-3-deoxy-1-thio-β-D-glucopyranoside 
• 139631-37-1 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose 
• 90852-19-0 (1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol-triacetat 
• 90899-14-2 (1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol 
• 236115-61-0 [(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate 
• 236115-66-5 3-azido-3-deoxy-2,4,6-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside 
• 236115-75-6 4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine 
• 144218-74-6 6-O-(4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 
• 103358-05-0 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine 

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.

Design and synthesis of new aminoglycoside antibiotics containing neamine as an optimal core structure: Correlation of antibiotic activity with in vitro inhibition of translation

The structure and activity of the pseudodisaccharide core found in aminoglycoside antibiotics was probed with a series of synthetic analogues in which the position of amino groups was varied around the glucopyranose ring. The naturally occurring structure

Synthesis of kanamycin A analogs containing 6-amino-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranose

6-Azido-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranoses were synthesized in five steps from (2S)- and (2R)-1,2-O-isopropylideneglycerols, respectively. After conversion into the corresponding ethyl 1-thioglycosides, each was condensed with a protected derivative of 6-O-(3-amino-3-deoxy-α-D-glucopyranosyl)-2-deoxystreptamine (16). Deprotection and reduction of the azido group of the condensation products gave the title compounds.

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'.