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25546-65-0

Basic Information
CAS No.: 25546-65-0
Name: RIBOSTAMYCIN SULFATE SALT
Article Data: 10
Molecular Structure:
Molecular Structure of 25546-65-0 (RIBOSTAMYCIN SULFATE SALT)
Formula: C17H34 N4 O10
Molecular Weight: 454.478
Synonyms: AntibioticSF 733; Dekamycin IV; Hetangmycin; NSC 138925; Ribostamycin; SF 733; Vistamycin
Density: 1.1751 (rough estimate)
Melting Point: 192-195°; mp 175-180° (dec)
Boiling Point: 561.28°C (rough estimate)
Safety: Poison by intravenous route. Moderately toxic by intramuscular and intraperitoneal routes. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
PSA: 345.36000
LogP: -3.42310
Synthetic route
28440-41-7, 64999-27-5, 64999-28-6

tetra-N-acetylribostamycin

25546-65-0

ribostamycin

Conditions
ConditionsYield
With hydrazine hydrate at 100℃; for 66h; sealed tube;59%
78763-89-0

1,3,2',6'-Tetra-N-(benzyloxycarbonyl)-2'',3'',5''-tri-O-benzoyl-6,3',4'-tri-O-benzylribostamycin

25546-65-0

ribostamycin

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; sodium methylate; acetic acid 1.) MeOH, 3.5 h, 2.) aq. dioxane, 48 h, then water; Yield given. Multistep reaction;
96181-96-3

[(1S,2R,3R,5R)-2-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-(acetylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-3-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-4,6-dihydroxy-5-nitro-cyclohexyl]-carbamic acid benzyl ester

25546-65-0

ribostamycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min
3: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube
View Scheme
96181-94-1

C41H53N3O23

25546-65-0

ribostamycin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: benzene; pyridine / 1 h / Heating
2: 62 percent / NaOMe / methanol; nitromethane / 14 h / Ambient temperature
3: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min
5: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube
View Scheme
96200-99-6

C55H66N4O18

25546-65-0

ribostamycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube
View Scheme
96181-92-9

C59H69N3O22

25546-65-0

ribostamycin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: pyridine
2: 1.) BF3-Et2O; 2.) Jones reagent / 1.) THF, 2 deg C, 40 min; 2.) r.t., 4 h
3: benzene; pyridine / 1 h / Heating
4: 62 percent / NaOMe / methanol; nitromethane / 14 h / Ambient temperature
5: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min
7: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube
View Scheme
96181-93-0

C61H71N3O23

25546-65-0

ribostamycin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) BF3-Et2O; 2.) Jones reagent / 1.) THF, 2 deg C, 40 min; 2.) r.t., 4 h
2: benzene; pyridine / 1 h / Heating
3: 62 percent / NaOMe / methanol; nitromethane / 14 h / Ambient temperature
4: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min
6: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube
View Scheme
96181-90-7

C43H57N3O23

25546-65-0

ribostamycin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 62 percent / NaOMe / methanol; nitromethane / 14 h / Ambient temperature
2: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min
4: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube
View Scheme
25546-65-0

ribostamycin

1064665-41-3

γ-L-Glu-((S)-4-amino-2-hydroxybutyryl)-N-acetylcysteamine thioester

1064665-42-4

γ-L-Glu-butirosin B

Conditions
ConditionsYield
With recombinant BtrH enzyme at 20℃; for 6h; pH=7.9; aq. buffer; Enzymatic reaction;100%
25546-65-0

ribostamycin

76-83-5

trityl chloride

1,3,2',6'-tetra-N-trityl-5''-mono-O-trityl-ribostamycin

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 72h;70%
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Chemistry

IUPAC Name: 5-Amino-2-(aminomethyl)-6-[4,6-diamino-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
The MF of Ribostamycin sulfate salt (CAS NO.25546-65-0) is C17H36N4O14S.

                              
The MW of Ribostamycin sulfate salt (CAS NO.25546-65-0) is 552.55.
Synonyms of Ribostamycin sulfate salt (CAS NO.25546-65-0): Ribostamycin disulfate ; Ribostamycin sulfate salt ; Ribostamycin sulphate ; Antibioticsf733 ; Dekamyciniv ; D-Ribofuranosyl-(1-5))-2-deoxy- ; Hetangmycin
Flash Point: 502.7 °C
Boiling Point: 907.6 °C
Storage temp: 2-8 °C
EINECS: 247-091-5

Toxicity Data With Reference

1.    

ipr-rat LD50:4400 mg/kg

    KSRNAM    Kiso to Rinsho. Clinical Report. 4 (1970),2464.
2.    

ivn-rat LD50:535 mg/kg

    KSRNAM    Kiso to Rinsho. Clinical Report. 4 (1970),2464.
3.    

ims-rat LD50:1850 mg/kg

    NKRZAZ    Chemotherapy (Tokyo). 32 (1984),949.
4.    

orl-mus LD50:7000 mg/kg

    85GDA2    CRC Handbook of Antibiotic Compounds. 1 (1980),141.
5.    

ipr-mus LD50:2830 mg/kg

    KSRNAM    Kiso to Rinsho. Clinical Report. 4 (1970),2464.
6.    

scu-mus LD50:3350 mg/kg

    KSRNAM    Kiso to Rinsho. Clinical Report. 4 (1970),2464.
7.    

ivn-mus LD50:300 mg/kg

    KSRNAM    Kiso to Rinsho. Clinical Report. 4 (1970),2464.
8.    

ims-mus LD50:1600 mg/kg

    85GDA2    CRC Handbook of Antibiotic Compounds. 1 (1980),141.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Poison by intravenous route. Moderately toxic by intramuscular and intraperitoneal routes. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.Safety information of Ribostamycin sulfate salt (CAS NO.25546-65-0):
Hazard Codes  ToxicT
Risk Statements 
61 May cause harm to the unborn child
20/21/22 Harmful by inhalation, in contact with skin and if swallowed
Safety Statements 
53 Avoid exposure - obtain special instruction before use
22 Do not breathe dust
36/37/39 Wear suitable protective clothing, gloves and eye/face protection
45 In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
WGK Germany  3
RTECS  WK2300000