CAS No.3947-65-7,(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL Suppliers

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Basic Information

Molecular Structure:
CAS No.:	3947-65-7
Name:	(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL
Article Data:	20

Formula:	C12H26 N4 O6
Molecular Weight:	322.362
Synonyms:	NeomycinA (6CI,7CI,8CI); (+)-Neamine; Dekamycin V; Neamin; Neamine; Nebramycin X; Negamicin;O-2,6-Diamino-2,6-dideoxy-a-D-glucopyranosyl-(1®4)-1,3-diamino-1,2,3-trideoxy-D-myo-inositol; ST 7
Density:	1.51g/cm³
Melting Point:	225.5°C (rough estimate)
Boiling Point:	577.9°C at 760 mmHg
Flash Point:	303.3°C
Safety:	Poison by intravenous route. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NO_x.
PSA:	203.46000
LogP:	-2.31440

Synthetic route

: 549501-35-1
(1S,2R,3R,4S,6R)-4,6-Diamino-3-((2R,3R,4R,5R,6R)-3-amino-6-aminomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

: 3947-65-7
neomycin A

Conditions

Conditions	Yield
With hydrogen; 20% palladium hydroxide on carbon In water; acetic acid	91%
With hydrogen; acetic acid; palladium dihydroxide

: 119-04-0
neomycin B

: 3947-65-7
neomycin A

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 6h; Heating;	82%
With hydrogenchloride In methanol for 4h; Reflux;	80%
Stage #1: neomycin B With hydrogenchloride; methanol for 16h; acidic methanolysis; Stage #2: With Amberlite IRA-400 (OH-) In methanol for 0.5h; Hydrolysis;	67%
With water Acidic conditions; Inert atmosphere;

: neomycin B trisulfate

: 3947-65-7
neomycin A

Conditions

Conditions	Yield
Stage #1: neomycin B trisulfate With hydrogenchloride In methanol for 6h; Heating; Stage #2: With ammonium hydroxide; ammonia In methanol Further stages.;	70%

: 4146-30-9, 25389-98-4, 28002-70-2, 34289-38-8, 92283-95-9
neomycin B trisulfate

: 3947-65-7
neomycin A

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 80℃; for 3h; pH=< 1;	67%

: 25389-98-4
neomycin B sulphate

A: 98-01-1
furfural

B: 36468-53-8
β-D-ribofuranose

C: 3947-65-7
neomycin A

D: 59433-00-0
2,6-dideoxy-2,6-diamino-D-glucose

E: (2R,3S,4R,5R,6R)-5-Amino-2-aminomethyl-6-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy)-tetrahydro-pyran-3,4-diol

Conditions

Conditions	Yield
Product distribution; Rate constant; Irradiation; multistep reaction, radiolytic degradation;

...Expand

: 25389-98-4
neomycin B sulphate

A: 98-01-1
furfural

B: 36468-53-8
β-D-ribofuranose

C: 3947-65-7
neomycin A

D: (2S,3R,4R,5S,6S)-3-Amino-6-aminomethyl-tetrahydro-pyran-2,4,5-triol

E: (2S,3S,4R,5R,6R)-5-Amino-2-aminomethyl-6-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy)-tetrahydro-pyran-3,4-diol

Conditions

Conditions	Yield
Product distribution; Rate constant; Irradiation; multistep reaction, radiolytic degradation;

...Expand

neomycin-B: neomycin-B

: 3947-65-7
neomycin A

Conditions

Conditions	Yield
With hydrogenchloride; methanol
With hydrogenchloride

: 171032-74-9
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 3947-65-7
neomycin A

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 90 percent / ZnI2 / 1,2-dichloro-ethane / 50 °C 2: 98 percent / NaOMe / methanol 3: 94 percent / pyridine 4: 100 percent / NaN3 / dimethylformamide / 80 °C 5: 86 percent / NaH / dimethylformamide 6: N-iodosuccinimide; silver trifluoromethanesulfonate / diethyl ether; CH2Cl2 / -20 °C 7: NaOMe / methanol 8: P(CH3)3; 0.1 N aq. NaOH / tetrahydrofuran 9: H2; aq. AcOH / 20 percent Pd(OH)2/C View Scheme

Yield

Multi-step reaction with 9 steps
1: 90 percent / ZnI2 / 1,2-dichloro-ethane / 50 °C
2: 98 percent / NaOMe / methanol
3: 94 percent / pyridine
4: 100 percent / NaN3 / dimethylformamide / 80 °C
5: 86 percent / NaH / dimethylformamide
6: N-iodosuccinimide; silver trifluoromethanesulfonate / diethyl ether; CH2Cl2 / -20 °C
7: NaOMe / methanol
8: P(CH3)3; 0.1 N aq. NaOH / tetrahydrofuran
9: H2; aq. AcOH / 20 percent Pd(OH)2/C
View Scheme

: 202462-37-1
phenyl 2-azido-2-deoxy-1-thio-α/β-D-glucopyranoside

: 3947-65-7
neomycin A

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 94 percent / pyridine 2: 100 percent / NaN3 / dimethylformamide / 80 °C 3: 86 percent / NaH / dimethylformamide 4: N-iodosuccinimide; silver trifluoromethanesulfonate / diethyl ether; CH2Cl2 / -20 °C 5: NaOMe / methanol 6: P(CH3)3; 0.1 N aq. NaOH / tetrahydrofuran 7: H2; aq. AcOH / 20 percent Pd(OH)2/C View Scheme

: 183875-22-1
phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside

: 3947-65-7
neomycin A

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 98 percent / NaOMe / methanol 2: 94 percent / pyridine 3: 100 percent / NaN3 / dimethylformamide / 80 °C 4: 86 percent / NaH / dimethylformamide 5: N-iodosuccinimide; silver trifluoromethanesulfonate / diethyl ether; CH2Cl2 / -20 °C 6: NaOMe / methanol 7: P(CH3)3; 0.1 N aq. NaOH / tetrahydrofuran 8: H2; aq. AcOH / 20 percent Pd(OH)2/C View Scheme

Raw Materials

119-04-0

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Chemistry

Product Name: Neomycin A
CAS: 3947-65-7
The Molecular formula of Neomycin A (CAS NO.3947-65-7): C₁₂H₂₆N₄O₆
The Molecular Weight of Neomycin A (CAS NO.3947-65-7): 322.36
The Molecular Structure of Neomycin A (CAS NO.3947-65-7):

Density: 1.51 g/cm³
Flash Point: 303.3 °C
Boiling Point: 577.9 °C at 760 mmHg
Index of Refraction: 1.649
Molar Refractivity: 77.41 cm³
Molar Volume: 212.4 cm³
Polarizability: 30.69×10^-24cm³
Surface Tension: 92.6 dyne/cm
Enthalpy of Vaporization: 99.33 kJ/mol
Vapour Pressure: 9.19E-16 mmHg at 25°C
Water Solubility: 1e+006(mg/L)at 25°C

History

Neomycin was discovered in 1949 by the microbiologist Selman Waksman and his student Hubert Lechevalier at Rutgers University. It is produced naturally by the bacterium Streptomyces fradiae

Toxicity Data With Reference

1.	scu-mus LD50:1250 mg/kg	85ERAY Antibiotics: Origin, Nature, and Properties. 1 (1978),664.
2.	ivn-mus LD50:320 mg/kg	85ERAY Antibiotics: Origin, Nature, and Properties. 1 (1978),664.
3.	ivn-mus LD50:125 mg/kg	JANTAJ Journal of Antibiotics. 27 (1974),677.

Safety Profile

Poison by intravenous route. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NO_x.

Specification

Neomycin A with CAS number of 3947-65-7 is also called for 2-Desoxy-4-O-(2,6-diamino-2,6-didesoxy-alpha-D-glucopyranosyl)-D-streptamin ; 4-18-00-07474 (Beilstein Handbook Reference) ; 4-O-(2,6-Diamino-2,6-dideoxy-alpha-D-glucopyranosyl)-2-deoxy-D-streptamine ; BRN 0026714 ; Dekamycin V ; Neamin ; Neamine ; Nebramycin X ; Negamicin ; UNII-5981U00LY0 . Neomycin is overwhelmingly used as a topical preparation, such as Neosporin. It can also be given orally, where it is usually combined with other antibiotics. Neomycin is not absorbed from the gastrointestinal tract, and has been used as a preventive measure for hepatic encephalopathy and hypercholesterolemia. By killing bacteria in the intestinal tract, it keeps ammonia levels low and prevents hepatic encephalopathy, especially prior to GI surgery. It has also been used to treat small intestinal bacterial overgrowth. It is not given intravenously, as neomycin is extremely nephrotoxic (causes kidney damage), especially compared to other aminoglycosides. The exception is when neomycin is included, in very small quantities, as a preservative in some vaccines - typically 0.025 mg per dose.