25546-65-0

Basic information

• Product Name: RIBOSTAMYCIN SULFATE SALT
• Synonyms: RIBOSTAMYCIN DISULFATE;RIBOSTAMYCIN SULFATE SALT;RIBOSTAMYCIN SULPHATE;antibioticsf733;dekamyciniv;d-ribofuranosyl-(1-5))-2-deoxy-;hetangmycin;ribostamycin
• CAS NO: 25546-65-0
• Molecular Formula: C₁₇H₃₄N₄O₁₀
• Molecular Weight: 552.55
• EINECS: 247-091-5
• Mol File: 25546-65-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 192-195°; mp 175-180° (dec)
• Boiling Point: 561.28°C (rough estimate)
• Appearance: /
• Density: 1.1751 (rough estimate)
• Refractive Index: 1.6700 (estimate)
• Storage Temp.: 2-8°C
• PKA: 7.70(at 25℃)
• CAS DataBase Reference: RIBOSTAMYCIN SULFATE SALT(CAS DataBase Reference)
• NIST Chemistry Reference: RIBOSTAMYCIN SULFATE SALT(25546-65-0)
• EPA Substance Registry System: RIBOSTAMYCIN SULFATE SALT(25546-65-0)

Safety Data

• Hazard Codes: T
• Statements: 61-20/21/22
• Safety Statements: 53-22-36/37/39-45
• WGK Germany: 3
• RTECS: WK2300000
• Hazardous Substances Data: 25546-65-0(Hazardous Substances Data)

Usage

Definition

ChEBI: An amino cyclitol glycoside that is 4,6-diaminocyclohexane-1,2,3-triol having a 2,6-diamino-2,6-dideoxy-alpha-D-glucosyl residue attached at position 1 and a beta-D-ribosyl residue attache at position 2. It is an antibiotic produced by Streptomyces ribosidificus (formerly S. thermoflavus).

InChI:InChI=1/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9?,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1

Synthetic route

tetra-N-acetylribostamycin (28440-41-7, 64999-27-5, 64999-28-6) → ribostamycin (25546-65-0)

Conditions	Yield
With hydrazine hydrate at 100℃; for 66h; sealed tube;	59%

1,3,2',6'-Tetra-N-(benzyloxycarbonyl)-2'',3'',5''-tri-O-benzoyl-6,3',4'-tri-O-benzylribostamycin (78763-89-0) → ribostamycin (25546-65-0)

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;

[(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 (96181-96-3) → ribostamycin (25546-65-0)

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

C41H53N3O23 (96181-94-1) → ribostamycin (25546-65-0)

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

C55H66N4O18 (96200-99-6) → ribostamycin (25546-65-0)

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

C59H69N3O22 (96181-92-9) → ribostamycin (25546-65-0)

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

C61H71N3O23 (96181-93-0) → ribostamycin (25546-65-0)

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

C43H57N3O23 (96181-90-7) → ribostamycin (25546-65-0)

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

ribostamycin (25546-65-0) + γ-L-Glu-((S)-4-amino-2-hydroxybutyryl)-N-acetylcysteamine thioester (1064665-41-3) → γ-L-Glu-butirosin B (1064665-42-4)

Conditions	Yield
With recombinant BtrH enzyme at 20℃; for 6h; pH=7.9; aq. buffer; Enzymatic reaction;	100%

ribostamycin (25546-65-0) + trityl chloride (76-83-5) → 1,3,2',6'-tetra-N-trityl-5''-mono-O-trityl-ribostamycin

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

ribostamycin (25546-65-0) + heptafluorobutyric Acid (375-22-4) → C-3-azidoribostamycin tri(heptafluorobutyric acid)

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%

ribostamycin (25546-65-0) + ATP (56-65-5) → C27H46N9O16P

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

ribostamycin (25546-65-0) + N-tertiarybutoxycarbonyl-β-alanine N-hydroxysuccinimide ester (32703-87-0) → [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 (693776-12-4)

endo-N-hydroxy-5-norbornene-2,3-dicarboximide O-bromoacetate (872054-82-5) + ribostamycin (25546-65-0) → 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	Yield
In water; acetonitrile at 20℃; for 0.166667h;
In water; acetonitrile for 0.166667h; Product distribution / selectivity;

ribostamycin (25546-65-0) → 6'-N-β-alanine-1,3,3'-N-guanidinoribostamycin

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

ribostamycin (25546-65-0) → C58H101N11O25 (693776-13-5)

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

ribostamycin (25546-65-0) + YALPETGK (950832-64-1) → C49H80N10O20 (950832-57-2)

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.

ribostamycin (25546-65-0) + YALPMTGK (950832-65-2) → C49H82N10O18S (950832-47-0)

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.

ribostamycin (25546-65-0) + acetylcoenzyme A (72-89-9) → 2'-N-acetyl-ribostamycin

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

ribostamycin (25546-65-0) + P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt (91183-98-1) → N-acetylglucosaminylribostamycin (1079925-74-8)

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;

ribostamycin (25546-65-0) → 5'-O-(4,4'-dimethoxytrityl)-1,3,2',6'-tetra-N-trifluoroacetylribostamycin (1315508-28-1)

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

ribostamycin (25546-65-0) + trifluoroacetic acid-methyl ester (431-47-0) → C25H30F12N4O14 (1315508-27-0)

Conditions	Yield
With triethylamine In methanol at 20℃;

Upstream product

• 28440-41-7 tetra-N-acetylribostamycin 
• 96181-90-7 C₄₃H₅₇N₃O₂₃ 
• 96181-93-0 C₆₁H₇₁N₃O₂₃ 
• 96181-92-9 C₅₉H₆₉N₃O₂₂ 
• 96200-99-6 C₅₅H₆₆N₄O₁₈ 
• 96181-94-1 C₄₁H₅₃N₃O₂₃ 
• 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 
• 78763-89-0 1,3,2',6'-Tetra-N-(benzyloxycarbonyl)-2'',3'',5''-tri-O-benzoyl-6,3',4'-tri-O-benzylribostamycin 

Downstream Products

• 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 
• 950832-57-2 C₄₉H₈₀N₁₀O₂₀ 
• 1079925-74-8 N-acetylglucosaminylribostamycin 
• 1315508-27-0 C₂₅H₃₀F₁₂N₄O₁₄ 
• 1315508-28-1 5'-O-(4,4'-dimethoxytrityl)-1,3,2',6'-tetra-N-trifluoroacetylribostamycin 
• 1064665-42-4 γ-L-Glu-butirosin B 
• 693776-13-5 C₅₈H₁₀₁N₁₁O₂₅ 

Relevant articles and documents

SYNTHESIS OF RIBOSTAMYCIN. AN APPLICATION OF A CHEMICAL CONVERSION METHOD FROM CARBOHYDRATE TO AMINOCYCLITOL

An aminoglycoside antibiotic ribostamycin was synthesized from D-glucosamine and ribose via an amino-trisaccharide intermediate, which was prepared through successive selective glycosidations on the 1,6-anhydro-D-glucosamine moiety.

Chemical modification of neamine. Part III.

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