• Name

  RIBOSTAMYCIN SULFATE SALT

• EINECS
• CAS No. 25546-65-0
• Article Data10
• CAS DataBase
• Density 1.1751 (rough estimate)
• Solubility
• Melting Point 192-195°; mp 175-180° (dec)
• Formula C17H34 N4 O10
• Boiling Point 561.28°C (rough estimate)
• Molecular Weight 454.478
• Flash Point
• Transport Information
• Appearance
• 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 NO_x.
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms AntibioticSF 733; Dekamycin IV; Hetangmycin; NSC 138925; Ribostamycin; SF 733; Vistamycin
• 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions

Yield

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

Conditions

Yield

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

Conditions	Yield
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

Conditions	Yield
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

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

25546-65-0

ribostamycin

375-22-4

heptafluorobutyric Acid

C-3-azidoribostamycin tri(heptafluorobutyric acid)

Conditions

Conditions	Yield
Stage #1: ribostamycin With 1H-imidazole-1-sulfonyl azide hydrochloride; sodium hydroxide In aq. phosphate buffer at 20℃; for 18h; pH=8; Stage #2: heptafluorobutyric Acid In acetone at 40℃; regioselective reaction;	44%

25546-65-0

ribostamycin

56-65-5

ATP

C27H46N9O16P

Conditions

Conditions	Yield
at 37℃; aminoglycoside-4'-nucleotidyltransferaze of Bacillus brevis, MgCl2, potassium phosphate buffer (pH 6.0);

25546-65-0

ribostamycin

32703-87-0

N-tertiarybutoxycarbonyl-β-alanine N-hydroxysuccinimide ester

693776-12-4

[2-({(2R,3S,4R,5R,6R)-5-Amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-3-hydroxy-cyclohexyloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl}-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

872054-82-5

endo-N-hydroxy-5-norbornene-2,3-dicarboximide O-bromoacetate

25546-65-0

ribostamycin

N-{(2R,3S,4R,5R,6R)-5-Amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-3-hydroxy-cyclohexyloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl}-2-bromo-acetamide

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; for 0.166667h;
In water; acetonitrile for 0.166667h; Product distribution / selectivity;

25546-65-0

ribostamycin

6'-N-β-alanine-1,3,3'-N-guanidinoribostamycin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: trifluoroacetic acid / CH2Cl2 View Scheme

25546-65-0

ribostamycin

693776-13-5

C58H101N11O25

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N View Scheme

25546-65-0

ribostamycin

950832-64-1

YALPETGK

950832-57-2

C49H80N10O20

Conditions

Conditions	Yield
With Tris-HCl buffer; 2-hydroxyethanethiol; transpeptidase sortase A from Staphylococcus aureus at 37℃; for 6h; pH=7.5; Enzymatic reaction;	21.7 % Chromat.

25546-65-0

ribostamycin

950832-65-2

YALPMTGK

950832-47-0

C49H82N10O18S

Conditions

Conditions	Yield
With Tris-HCl buffer; 2-hydroxyethanethiol; transpeptidase sortase A from Staphylococcus aureus at 37℃; for 6h; pH=7.5; Enzymatic reaction;	22.1 % Chromat.

25546-65-0

ribostamycin

72-89-9

acetylcoenzyme A

2'-N-acetyl-ribostamycin

Conditions

Conditions	Yield
With MES buffer at 20℃; for 16h; pH=6;

25546-65-0

ribostamycin

91183-98-1

P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt

1079925-74-8

N-acetylglucosaminylribostamycin

Conditions

Conditions	Yield
With Neo 15 protein expressed with an N-terminal His6-tag in Escherichia coli BL21 (DE3), the mass = 41295 Da (including the His6-tag and with loss of N-terminal methionine), glycosyltransferase at 30℃; pH=8.4; aq. buffer; Enzymatic reaction;

25546-65-0

ribostamycin

1315508-28-1

5'-O-(4,4'-dimethoxytrityl)-1,3,2',6'-tetra-N-trifluoroacetylribostamycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / methanol / 20 °C 2: pyridine View Scheme

25546-65-0

ribostamycin

431-47-0

trifluoroacetic acid-methyl ester

1315508-27-0

C25H30F12N4O14

Conditions

Conditions	Yield
With triethylamine In methanol at 20℃;

XYLOSTATIN Chemical Properties

XYLOSTATIN Toxicity Data With Reference

XYLOSTATIN Consensus Reports

XYLOSTATIN Safety Profile