2-[(4R,6S,7R,9R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

Base Information

• Chemical Name: 2-[(4R,6S,7R,9R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
• CAS No.: 1401-69-0
• Molecular Formula: C46H77NO17
• Molecular Weight: 916.114
• Hs Code.: 2941906000
• European Community (EC) Number: 215-754-8
• Wikipedia: Tylosin
• NCI Thesaurus Code: C84234
• RXCUI: 995505
• Mol file: 1401-69-0.mol

Synonyms:Tylosin

Chemical Property of 2-[(4R,6S,7R,9R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

Chemical Property:

• Appearance/Colour: COA
• Melting Point: 18-132oC
• Refractive Index: 1.5280 (estimate)
• Boiling Point: 980.7 °C at 760 mmHg
• PKA: pKa 7.73(H2O t = 25 I = 0.167) (Uncertain)
• Flash Point: 546.9 °C
• PSA: 238.67000
• Density: 1.24 g/cm³
• LogP: 1.83350
• Storage Temp.: 2-8°C
• Water Solubility.: H2O: soluble 50 mg/mL
• XLogP3: 1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 13
• Exact Mass: 915.51914999
• Heavy Atom Count: 64
• Complexity: 1560

Purity/Quality:

99% ^*data from raw suppliers

Tylosin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N
• Statements: 42/43-50
• Safety Statements: 36-61-45-36/37-22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Animal Feed Additives
• Canonical SMILES: CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)C)COC4C(C(C(C(O4)C)O)OC)OC
• Isomeric SMILES: CC[C@@H]1C(C=C(C=CC(=O)[C@@H](C[C@@H]([C@@H](C([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)C)COC4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
• Description: Occupational exposure concerns farmers, breeders, animal-feed workers and veterinarians. Tylosin is a macrolide antibiotic produced by S. fradiae that has bacteriostatic activity against Gram-positive bacteria. It is a mixture of tylosin A, B, C, and D, with tylosin A contributing 80% of its bacteriostatic activity. Tylosin has MIC values of 9.6, 16.4, 0.1, 1, and 0.5 μg/ml for F. necrophorum, A. pyogenes, M. gallisepticum, S. aureus, and S. uberis, respectively.,, Formulations containing tylosin have been used for the prevention of liver abscesses in cattle. Tylosin is an environmental contaminant because it is not fully metabolized by treated livestock and enters the environment through manure-based fertilizers.
• Uses: paramagnetic agent Tylosin is a 16-membered macrocyclic lactone isolated from Streptomyces fradiae in 1961. Tylosin has broad spectrum antibacterial activity and was developed as a veterinary pharmaceutical for treatment of bacterial infections in a range of domestic animals . Tylosin acts by binding to the 50S ribosomal subunit resulting in the inhibition of protein synthesis in bacteria. Macrolide antibiotic isolated from a strain of Streptomycetes fradiae found in soil from Thailand. Antibacterial.
• Indications: In cattle, tylosin is used for treatment of BRD caused by Mannheimia, Pasteurella multocida, and Histophilus somni (formerly Haemophilus somnus). It is used for interdigital necrobacillosis (foot rot) in cattle caused by Fusobacterium necrophorum or Bacteroides melaninogenicus. In pigs, it is used for treatment of swine arthritis caused by Mycoplasma hyosynoviae, swine pneumonia caused by Pasteurella spp., swine erysipelas caused by Erysipelothrix rhusiopathiae, swine dysentery associated with Serpulina (Treponema) hyodysenteriae, and proliferative enteropathy caused by L. intracellularis. For treatment in pigs, it is also added to feed (Type A–medicated feed article) or drinking water. In small animals, it is used for gram-positive soft tissue and skin infections. However, the most common use in dogs is for treatment of diarrhea, referred to as antibiotic-responsive diarrhea, that has not responded to other treatments. The etiology of the diarrhea is not known but may be caused by Clostridium or Camphylobacter. For this use, the powdered formulation (swine formulation) is most often added to food daily for maintenance.

Technology Process of 2-[(4R,6S,7R,9R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

There total 21 articles about 2-[(4R,6S,7R,9R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

C50H81NO19 (84120-92-3,84171-63-1) → tylosin (1401-69-0)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(00)87619-4

Reference yield: 47.0%

C48H81NO18S (112389-05-6,112456-97-0) → tylosin (1401-69-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃;

Reference yield:

→ desmycosin (1401-69-0)

Guidance literature:

upstream raw materials:

C₅₀H₈₁NO₁₉

C₄₈H₈₁NO₁₈S

4-O-acetylmycarose

4-O-acetyl-1,5-anhydro-2,6-dideoxy-3-C-methyl-L-ribo-hex-1-enitol

Downstream raw materials:

demycarosyltylosin

(11R)-20-deoxo-10,11-dihydro-11-phenylthiotylosin 20-diphenylthioacetal

tylonolide 5,20-hemiacetal

5-O-mycaminosylprotylonolide

Refernces

• 1、 -. "Method for using tylosin D as raw material to prepare tilmicosin". Paragraph 0058; 0059; 0060. . Retrieved 2017/07/20.
• 2、 Tatsuta, Kuniaki,Amemiya, Yoshiya,Kanemura, Yoshinobu,Takahashi, Hideaki,Kinoshita, Mitsuhiro. "TOTAL SYNTHESIS OF TYLOSIN". . p. 3375 - 3378. Retrieved 2007/10/02.