11032-98-7

Basic information

• Product Name: tylosin B
• Synonyms: tylosin B;4'-O-De(2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranosyl)tyrosine [antibiotic];5-O-De[4-O-(3-C-methyl-2,6-dideoxy-α-L-ribo-hexopyranosyl)-3-(dimethylamino)-3,6-dideoxy-β-D-glucopyranosyl]-5-O-[3-(dimethylamino)-3,6-dideoxy-β-D-glucopyranosyl]tyrosine [antibiotic];Demycarosyltylosin;Desmycosin;4A-O-De(2,6-dideoxy-3-C-Methyl-α-L-ribo-hexopyranosyl)tylosin;2-((4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-(((2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-16-ethyl-4-hydroxy-15-((((2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methy
• CAS NO: 11032-98-7
• Molecular Formula: C₃₉H₆₅NO₁₄
• Molecular Weight: 771.9317
• Product Categories: Carbohydrates & Derivatives;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Carbohydrates & Derivatives, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 11032-98-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 114-116 °C(Solv: chloroform (67-66-3))
• Boiling Point: 896.7°Cat760mmHg
• Flash Point: 496.1°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.541
• PKA: pKa 8.36(H2O t=25.0 I=0.167) (Uncertain)
• CAS DataBase Reference: tylosin B(CAS DataBase Reference)
• NIST Chemistry Reference: tylosin B(11032-98-7)
• EPA Substance Registry System: tylosin B(11032-98-7)

Safety Data

• Hazardous Substances Data: 11032-98-7(Hazardous Substances Data)

Usage

Description

Tylosin B is a 16-membered macrolide antibiotic and a metabolite of Tylosin (T947650). It is also a precursor to Tilmicosin (T440500) and is characterized by its off-white solid chemical properties.

Uses

Used in Pharmaceutical Industry:
Tylosin B is used as an antibiotic agent for treating bacterial infections in both humans and animals. Its macrolide structure allows it to target and inhibit bacterial protein synthesis, leading to the disruption of essential cellular functions and ultimately the death of the bacteria.
Used in Veterinary Medicine:
In the veterinary field, tylosin B is used as a growth promoter and therapeutic agent to prevent and treat respiratory diseases, enteric infections, and other bacterial infections in livestock. Its use helps to maintain the overall health and productivity of animals in the industry.
Used in Agricultural Industry:
Tylosin B can also be utilized in agriculture as a biocontrol agent to protect crops from bacterial infections. By incorporating tylosin B into agricultural practices, it can help to reduce the reliance on chemical pesticides and promote more sustainable farming methods.
Used in Research and Development:
In the scientific community, tylosin B serves as a valuable compound for research and development purposes. Its unique structure and properties make it an interesting subject for studying antibiotic resistance, drug interactions, and the development of new antimicrobial agents.

InChI:InChI=1/C39H65NO14/c1-11-29-26(19-50-39-37(49-10)36(48-9)33(46)24(6)52-39)16-20(2)12-13-27(42)21(3)17-25(14-15-41)35(22(4)28(43)18-30(44)53-29)54-38-34(47)31(40(7)8)32(45)23(5)51-38/h12-13,15-16,21-26,28-29,31-39,43,45-47H,11,14,17-19H2,1-10H3/b13-12+,20-16+/t21-,22+,23-,24-,25+,26-,28-,29-,31+,32-,33-,34-,35-,36-,37-,38+,39-/m1/s1

Synthetic route

tylosin (1401-69-0) → tylosin B (11032-98-7)

Conditions	Yield
With hydrogenchloride In water at 35℃; for 2h;	100%
With hydrogenchloride at 20℃; for 4h;	95%
With hydrogenchloride at 20℃; for 96h; pH=2.8;	91.6%

tylosin (1401-69-0) → 2,4,6-trideoxy-3-methyl-α,β-L-ribo-hexopyranose (18423-82-0, 20108-38-7, 26391-83-3, 98168-04-8, 98168-07-1, 98168-10-6, 98168-11-7) + tylosin B (11032-98-7)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 25℃;	A n/a B 90%

tylosin A tartrate → tylosin B (11032-98-7)

Conditions	Yield
With hydrogenchloride In water for 4h;	70.45%

10,13-dihydro-13-hydroxy-desmycosin-20-dimethyl acetal (198077-17-7) → tylosin B (11032-98-7) + 10,13-dihydro-13-hydroxy-desmycosin

Conditions	Yield
With trifluoroacetic acid In acetonitrile at 20℃; for 2h; Hydrolysis; dehydration;	A 35% B 35%

desmycosin 20-dimethyl acetal (94591-58-9) → tylosin B (11032-98-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: m-ClPBA / CH2Cl2 / 7 h / 20 °C 2: 10.1 g / Ph3P / ethyl acetate / 2 h / Heating 3: 65 percent / ammonium chloride; Zn / ethanol; H2O / 20 °C 4: 35 percent / aq. trifluoroacetic acid / acetonitrile / 2 h / 20 °C View Scheme

12,13-epoxydesmycosin-20-dimethylacetal (198077-05-3) → tylosin B (11032-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / ammonium chloride; Zn / ethanol; H2O / 20 °C 2: 35 percent / aq. trifluoroacetic acid / acetonitrile / 2 h / 20 °C View Scheme

C41H71NO17 → tylosin B (11032-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 10.1 g / Ph3P / ethyl acetate / 2 h / Heating 2: 65 percent / ammonium chloride; Zn / ethanol; H2O / 20 °C 3: 35 percent / aq. trifluoroacetic acid / acetonitrile / 2 h / 20 °C View Scheme

20-dihydrotylosin (1404-48-4) → tylosin B (11032-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite / ethyl acetate / 6 h / 0 - 5 °C 2: hydrogenchloride / water / 0.5 h / 50 °C View Scheme

tylosin B (11032-98-7) → 20-dihydrodesmycosin (66799-85-7)

Conditions	Yield
With sodium tetrahydroborate In water; isopropyl alcohol for 0.5h;	96%
With sodium tetrahydroborate; water In isopropyl alcohol at 20℃; for 0.5h;	95%
With sodium tetrahydroborate In water; isopropyl alcohol at 20℃; for 0.5h;	95%
With sodium tetrahydroborate In methanol at 25℃; for 20h; pH 7.5;	76%

N-benzyl-N-([1-(3-quinolyl)-1H-1,2,3-triazol-4-yl]methyl)amine + tylosin B (11032-98-7) → 20-deoxy-20-{N-benzyl-N-[1-(3-quinolyl)-1H-1,2,3-triazol-4-yl]methylamino}-desmycosin

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃;	90%

acetic anhydride (108-24-7) + tylosin B (11032-98-7) → 2',4'-di-O-acetyldesmycosin (56858-50-5)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	85.5%
In dichloromethane at 20℃; for 2.5h;

tylosin B (11032-98-7) + ethylene glycol (107-21-1) → desmycosin 20-(ethylene acetal) (91661-73-3)

Conditions	Yield
With camphor-10-sulfonic acid In acetonitrile for 1h; Ambient temperature;	80%

tylosin B (11032-98-7) + thioacetic acid (507-09-5) → 3C41H69NO15S*CHCl3 + 2C41H69NO15S*CHCl3

Conditions	Yield
1.) CH2Cl2, 25 deg C, 40 h; 2.) methanol, 25 deg C, 72 h; Yield given. Multistep reaction;	A 75% B n/a
1.) CH2Cl2, 25 deg C, 40 h; 2.) methanol, 25 deg C, 72 h; Yield given. Multistep reaction;	A n/a B 3%

ethanol (64-17-5) + tylosin B (11032-98-7) → desmycosin-20-diethylketal (80241-17-4)

Conditions	Yield
With toluene-4-sulfonic acid for 1h;	75%

tylosin B (11032-98-7) → 19-deformyldesmycosin (78740-70-2)

Conditions	Yield
With Wilkinson's catalyst In benzene at 90℃; for 16h;	73%

tylosin B (11032-98-7) + 2-(3,4-diaminophenyl)-imidazoline (66639-63-2) → 20-[5-(2-imidazolinyl)-2-benzimidazolyl]desmycosin hydrochloride

Conditions	Yield
With p-benzoquinone In ethanol for 4h; Heating;	73%

tylosin B (11032-98-7) + ethylene glycol (107-21-1) → C43H73NO16 (138146-90-4)

Conditions	Yield
With camphor-10-sulfonic acid; orthoformic acid triethyl ester In toluene; acetonitrile for 5h; Ambient temperature;	66%

diazomethane (186581-53-3, 908094-01-9) + tylosin B (11032-98-7) → C41H69N3O14 (112389-25-0)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 25℃;	65%

tylosin B (11032-98-7) + thiophenol (108-98-5) → 3C45H71NO14S*CHCl3 + 3C45H71NO14S*CHCl3

Conditions	Yield
at 25℃; for 48h;	A 47% B 47%

acetic anhydride (108-24-7) + tylosin B (11032-98-7) → 2',4',4"-tri-O-acetyldesmycosin (112389-48-7)

Conditions	Yield
With pyridine at 25℃; for 74h;	46%
In pyridine at 25℃; for 124h;	39%

tylosin B (11032-98-7) → 10,11-dihydrodesmycosin + desmycosin dimer

Conditions	Yield
In phosphate buffer at 20℃; pH=5.3; Product distribution; Electrolysis;	A 30% B 44%

tylosin B (11032-98-7) + 4-[N-(N-morpholinyl)]amidino-1,2-phenylenediamine (433233-94-4) → 20-[5-(N-morpholinylamidino)-2-benzimidazolyl]desmycosin hydrochloride

Conditions	Yield
With p-benzoquinone In ethanol for 4h; Heating;	37%

tylosin B (11032-98-7) + 4-(N-isopropylamidino)-1,2-phenylene diamine (148344-30-3) → 20-[5-(N-isopropylamidino)-2-benzimidazolyl]desmycosin hydrochloride

Conditions	Yield
With p-benzoquinone In ethanol for 4h; Heating;	36%

tylosin B (11032-98-7) → desmycosin 8β,20α-aldol (112389-51-2, 112457-08-6)

Conditions	Yield
With potassium carbonate In methanol; water at 25℃; for 18h;	35%

methanol (67-56-1) + tylosin B (11032-98-7) → methyl 5-β-D-desosaminyloxy-5-<2-formyl-3-(6-hydroxy-3-methyl-5-β-D-mycinosyloxyocta-1,3-dienyl)-4-methylcyclopenta-2-dienyl>-3-hydroxy-4-methylvalerate (122825-60-9)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 25℃; for 49h;	29%

Boc-Aoac-(Gly-Pro)3-OBzl (1235514-69-8) + tylosin B (11032-98-7) → C69H104N8O22 (1235514-51-8)

Conditions	Yield
Stage #1: Boc-Aoac-(Gly-Pro)3-OBzl With trifluoroacetic acid at 20℃; for 1h; Stage #2: tylosin B In dimethyl sulfoxide at 50℃; for 12h; pH=4.7; sodium acetate buffer;	26%

Boc-Aoac-Ala-Ala-Phe-Ala-Ala-Phe-Lys-OMe + tylosin B (11032-98-7) → C74H118N10O23

Conditions	Yield
Stage #1: Boc-Aoac-Ala-Ala-Phe-Ala-Ala-Phe-Lys-OMe With trifluoroacetic acid at 20℃; for 1h; Stage #2: tylosin B In dimethyl sulfoxide at 50℃; for 12h; pH=4.7; sodium acetate buffer;	23%

Boc-Aoac-Ala-Ala-Phe-Ala-Ala-Phe-Lys(Z)-OMe + tylosin B (11032-98-7) → C82H124N10O25

Conditions	Yield
Stage #1: Boc-Aoac-Ala-Ala-Phe-Ala-Ala-Phe-Lys(Z)-OMe With trifluoroacetic acid at 20℃; for 1h; Stage #2: tylosin B In dimethyl sulfoxide at 50℃; for 12h; pH=4.7; sodium acetate buffer;	21%

Boc-Aoac-Phe-OEt (1235514-66-5) + tylosin B (11032-98-7) → C52H81N3O17 (1235514-48-3)

Conditions	Yield
Stage #1: Boc-Aoac-Phe-OEt With trifluoroacetic acid at 20℃; for 1h; Stage #2: tylosin B In dimethyl sulfoxide at 50℃; for 12h; pH=4.7; sodium acetate buffer;	20%

Boc-Aoac-(Ala)5-OMe (1235514-67-6) + tylosin B (11032-98-7) → C57H95N7O21 (1235514-49-4)

Conditions	Yield
Stage #1: Boc-Aoac-(Ala)5-OMe With trifluoroacetic acid at 20℃; for 1h; Stage #2: tylosin B In dimethyl sulfoxide at 50℃; for 12h; pH=4.7; sodium acetate buffer;	18%

L-tyrosine (60-18-4) + tylosin B (11032-98-7) → C48H74N2O16 (1235514-56-3)

Conditions	Yield
With sodium methylate In methanol at 20℃; for 12h; Molecular sieve;	18%

L-cysteine ethyl ester hydrochloride (868-59-7) + tylosin B (11032-98-7) → deformyl-19-(4-carbethoxy-2-thiazolidinyl)desmycosin (115033-47-1)

Conditions	Yield
In acetonitrile for 0.5h; Ambient temperature;

tylosin B (11032-98-7) → O-mycinosyltylonolide (80879-01-2)

Conditions	Yield
With pyridine; methanol; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride Yield given. Multistep reaction;

tylosin B (11032-98-7) + 3,5-bis(trifluoromethyl)piperidine → 20-Deoxo-20-(3,5-bis(trifluoromethyl)piperidynyl)desmycosin

Conditions	Yield
With sodium cyanoborohydride 1.) EtOH, r.t., 45 min, 2.) r.t., 5 h; Yield given. Multistep reaction;

Upstream product

• 1401-69-0 tylosin 
• 1401-69-0 15-[[(6-deoxy-2,6-di-O-methyl-β-D-allopyranosyl)-oxy]methyl]-6-[[3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-α-L-ribo-hexapyranosyl)-3-(dimethylamino)-β-D-glucopyranosyl]oxy]-16-ethyl-4-hydroxy-5,9,13-trimethyl-2,10-oxo-oxocyclo-hexadeca-11,13-diene-7... 
• 1404-48-4 20-dihydrotylosin 
• 198077-17-7 10,13-dihydro-13-hydroxy-desmycosin-20-dimethyl acetal 
• 198077-05-3 12,13-epoxydesmycosin-20-dimethylacetal 
• 94591-58-9 desmycosin 20-dimethyl acetal 

Downstream Products

• 121231-05-8 2',4',4''-tri-O-acetyl-19-deformyl-3-O-(4-O-phenoxyacetyl-α-L-cladinosyl)desmycosin 
• 121230-89-5 2',4',4''-tri-O-acetyl-3-O-(4-O-phenoxyacetyl-α-L-cladinosyl)desmycosin 
• 1438281-50-5 20-(4-(4-pentyloxyphenyl)-1H-1,2,3-triazol-1-yl)-20-deoxodesmycosin 
• 1235514-56-3 C₄₈H₇₄N₂O₁₆ 
• 1235514-48-3 C₅₂H₈₁N₃O₁₇ 
• 50507-46-5 deepoxycirramycin A1 
• 81661-90-7 5-O-mycaminosylprotylonolide 
• 61219-81-6 tylonolide 5,20-hemiacetal 
• 81661-88-3 8,20-cyclo-20-hydroxy-5-O-mycaminosyltylonolide 
• 61257-02-1 5-O-mycaminosyltylonolide 
• 122825-60-9 methyl 5-β-D-desosaminyloxy-5-<2-formyl-3-(6-hydroxy-3-methyl-5-β-D-mycinosyloxyocta-1,3-dienyl)-4-methylcyclopenta-2-dienyl>-3-hydroxy-4-methylvalerate 

Relevant articles and documents

Peptide derivatives of tylosin-related macrolides

Approaches to the synthesis of model compounds based on the tylosin-related macrolides desmycosin and O-mycaminosyltylonolide were developed to study the conformation and topography of the nascent peptide chain in the ribosome tunnel using specially designed peptide derivatives of macrolide antibiotics. A method for selective bromoacetylation of desmycosin at the hydroxyl group of mycinose was developed, which involves preliminary acetylation of mycaminose. The reaction of the 4″-bromoacetyl derivative of the antibiotic with cesium salts of the dipeptide Boc-Ala-Ala-OH and the hexapeptide MeOTr-Gly-Pro-Gly-Pro- Gly-Pro-OH led to the corresponding peptide derivatives of desmycosin. The protected peptides Boc-Ala-Ala-OH, Boc-Ala-Ala-Phe-OH, and Boc-Gly-Pro-Gly-Pro- Gly-Pro-OH were condensed with the C23-hydroxyl group of O- mycaminosyltylonolide.

New dihydro and tetrahydro derivatives of desmycosin. III. The opening of oxirane ring of 12,13-epoxydesmycosin

Opening the oxirane ring of 12,13-epoxydesmycosin dimethylacetal (1) by catalytic hydrogenation gave the 10,11-dihydro-12,13-epoxy derivative (3) as the main product. Reductive oxirane cleavage was accomplished with dissolved metal (Zn) giving the 10,13-dihydro-13-hydroxy compound (6). Mild acid hydrolysis of 6 gave expected 10,13-dihydro-13-hydroxydesmycosin (8), but hydrolysis of 3, under the same conditions, gave three tautomeric desepoxy products.

TYLOSIN DERIVATIVES AND METHOD FOR PREPARATION THEREOF

The present invention relates to new macrolide derivatives, in particular new tylosin derivatives of the formula (Ila), a pharmaceutical or veterinary composition comprising the derivatives; a method for preparation thereof; a method for treating and/or preventing bacterial infections in an animal, wherein the method comprises administering the derivatives or the composition; and a use of the derivatives for the manufacture of medicaments for treating and/or preventing bacterial infections in an animal.

3,6-BRIDGED TYLOSIN DERIVATIVES

The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.