103358-05-0

Basic information

• Product Name: 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine
• Synonyms: 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine
• CAS NO: 103358-05-0
• Molecular Weight: 785.915
• Mol File: 103358-05-0.mol

Chemical Properties

• CAS DataBase Reference: 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine(103358-05-0)
• EPA Substance Registry System: 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine(103358-05-0)

Safety Data

• Hazardous Substances Data: 103358-05-0(Hazardous Substances Data)

Upstream product

• 107-21-1 ethylene glycol 
• 144218-67-7 3',4'-anhydro-6'-N-(benzyloxycarbonyl)-4'-epi-1,3,3''-tri-N-tosylkanamycin A 
• 179533-31-4 1,3,6',3''-tetra-N-tosylkanamycin A 
• 98-59-9 p-toluenesulfonyl chloride 
• 133-92-6 kanamycin A sulfate 
• 144218-66-6 2''-O-acetyl-6'-N-(benzyloxycarbonyl)-4'-O-(benzylsulfonyl)-1,3,3''-tri-N-tosylkanamycin A 

Downstream Products

• 20744-51-8 6-O-[(3-deoxy-3-amino)-α-D-glucopyranosyl]-2-deoxy-streptamine 
• 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 
• 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 
• 179533-33-6 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 
• 143084-94-0 6-O-(2-O-Benzylsulfonyl-3-deoxy-4,6-O-isopropylidene-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-4,5-O-isopropylidene-1,3-di-N-tosylstreptamine 
• 143084-95-1 2-Deoxy-6-O-(2,3-dideoxy-4,6-O-isopropylidene-2,3-N-tosylepimino-α-D-mannopyranosyl)-4,5-O-isopropylidene-1,3-di-N-tosylstreptamine 
• 143084-96-2 2-Deoxy-6-O-(2,3-dideoxy-2,3-N-tosylepimino-α-D-mannopyranosyl)-1,3-di-N-tosylstreptamine 
• 143084-93-9 2-Deoxy-6-O-(3-deoxy-4,6-O-isopropylidene-3-tosylamido-α-D-glucopyranosyl)-4,5-O-isopropylidene-1,3-di-N-tosylstreptamine 

Relevant articles and documents

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'.