ChemicalBook CAS DataBase List NETILMICIN

NETILMICIN synthesis

4synthesis methods

Product Name:NETILMICIN
CAS Number:56391-56-1
Molecular formula:C21H41N5O7
Molecular Weight:475.58

Netilmicin, O-3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl (1→4)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl]-(1→6)- 2-deoxy-N3 -ethyl-L-streptamine (3.4.10), is also a semisynthetic antibiotic that is synthesized in two stages from another known antibiotic, sisomicin (3.4.11), which is produced by a culture of M. inyoensis. In the first stage of synthesis, reacting sisomicin with acetaldehyde in a specific acidic medium of pH 5 is successful in selectively giving an imine at the 3-amino group of the 2-deoxystreptamine region of the molecule. The resulting imine is then hydrogenated by sodium cyanoborohydride to an ethylamino derivative —netilmicin (32.4.12).

32385-11-8
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Yield:-

Steps:

Multi-step reaction with 3 steps
1: 1.) cupric acetate dihydrate / 1.) water/N,N-dimethylformamide, rt., 35 min, 2.) DMF, 30 min
2: 1.) 0.1 M HCl, 2.) sodium cyanoborohydride, 0.1 M HCl,3.) Amberlite IRA-401S (1-)> / 1.) water, 3 deg C, pH=2.7, 2.) oxolane/water, pH=2.7, rt., 18 h, 3.) pH=9, 1 h
3: 90 percent / M sodium hydroxide / 48 h / Heating

References:

Nagabhushan, Tattanahalli L.;Turner, William N.;Tsai, Hsinghan;Jaret, Robert S.;Schumacher, Doris;et al. [Carbohydrate Research,1984,vol. 130,p. 243 - 250]

D-Streptamine, O-2,6-bis(acetylamino)-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1→4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)]-N3-acetyl-2-deoxy-N1-ethyl- (9CI)

66567-31-5
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56391-56-1
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References

66065-86-9
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56391-56-1
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References

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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References

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