Trobicin

Base Information

• Chemical Name: Trobicin
• CAS No.: 21736-83-4
• Molecular Formula: C14H26Cl2N2O7
• Molecular Weight: 405.276
• Hs Code.: 3004909090
• European Community (EC) Number: 244-554-3
• NCI Thesaurus Code: C90690
• Mol file: 21736-83-4.mol

Synonyms:Actinospectacin;Adspec;Ferkel Spectam;Kempi;Prospec;Salmosan T;Salmosan-T;Spectam;Spectam, Ferkel;Spectinomycin;Spectinomycin Dihydrochloride, Anhydrous;Spectinomycin Dihydrochloride, Pentahydrate;Spectinomycin Hydrochloride;Stanilo;Trobicin

Chemical Property of Trobicin

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 5.05E-16mmHg at 25°C
• Melting Point: 194 °C
• Refractive Index: 1.586
• Boiling Point: 583.1 °C at 760 mmHg
• Flash Point: 306.4 °C
• PSA: 129.51000
• Density: 1.43g/cm3
• LogP: -0.53980
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear, faintly yellow
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 404.1117066
• Heavy Atom Count: 25
• Complexity: 478

Purity/Quality:

99% , ^*data from raw suppliers

SpectinomycinDihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC(=O)C2(C(O1)OC3C(C(C(C(C3O2)[NH2+]C)O)[NH2+]C)O)O.[Cl-].[Cl-]
• Isomeric SMILES: C[C@@H]1CC(=O)[C@]2([C@@H](O1)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H]([C@H]3O2)[NH2+]C)O)[NH2+]C)O)O.[Cl-].[Cl-]
• Uses: SPECTINOMYCIN DIHYDROCHLORIDE is an antibiotic used in the treatment and control of infectious bacterial enteritis in animals. Used in drug testing against nonreplicating mycobacterium tuberculosis. Antibacterial;Ribosomal protein
• Clinical Use: The aminocyclitol antibiotic spectinomycin hydrochloride(Trobicin), isolated from Streptomyces spectabilis andonce called actinospectocin, was first described by Lewisand Clapp. Its structure and absolute stereochemistryhave been confirmed by x-ray crystallography. It occursas the white, crystalline dihydrochloride pentahydrate,which is stable in the dry form and very soluble in water.Solutions of spectinomycin, a hemiacetal, slowly hydrolyzeon standing and should be prepared freshly andused within 24 hours. It is administered by deep intramuscularinjection.Spectinomycin is a broad-spectrum antibiotic withmoderate activity against many Gram-positive and Gramnegativebacteria. It differs from streptomycin and thestreptamine-containing aminoglycosides in chemical and antibacterialproperties. Like streptomycin, spectinomycininterferes with the binding of transfer RNA (tRNA) to the ribosomesand thus with the initiation of protein synthesis.Unlike streptomycin or the streptamine-containing antibiotics,however, it does not cause misreading of the messenger.Spectinomycin exerts a bacteriostatic action and isinferior to other aminoglycosides for most systemic infections.Currently, it is recommended as an alternative to penicillinG salts for the treatment of uncomplicated gonorrhea.A cure rate of more than 90% has been observed in clinicalstudies for this indication. Many physicians prefer to use atetracycline or erythromycin for prevention or treatment ofsuspected gonorrhea in penicillin-sensitive patients because,unlike these agents, spectinomycin is ineffective againstsyphilis. Furthermore, it is considerably more expensive thanerythromycin and most of the tetracyclines.

Technology Process of Trobicin

There total 7 articles about Trobicin 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: 90.0%

N,N'-<(benzyloxy)carbonyl>spectinomycin (56733-83-6,58560-43-3,68889-80-5) → (+)-spectinomycin dihydrochloride (21736-83-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; isopropyl alcohol;

DOI:10.1139/v85-026

Reference yield:

4-O-acetyl-N,N'-<(benzyloxy)carbonyl>-4(R)-dihydrospectinomycin (96681-00-4) → (+)-spectinomycin dihydrochloride (21736-83-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1N sodium methoxyde (pH 8); 2.) Dowex-50 (H+) / methanol / 0.25 h / 25 °C

2: 80 percent / 1.) bis(tri-n-butyltin)oxide, 2.)NBS / benzene / 25 °C / 1.) 1 h, 2.) 10 h

3: 90 percent / H₂ / palladium-on-charcoal / H₂O; propan-2-ol

With N-Bromosuccinimide; Dowex-50 (H+); hydrogen; sodium methylate; bis(tri-n-butyltin)oxide; palladium on activated charcoal; In methanol; water; isopropyl alcohol; benzene;

DOI:10.1139/v85-026

Reference yield:

Carbonic acid (1R,2S,3R,4R,5S,6R)-2,4-bis-(benzyloxycarbonyl-methyl-amino)-6-((2S,3R,4R,6R)-3,4-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,5-bis-(2,2,2-trichloro-ethoxycarbonyloxy)-cyclohexyl ester 2,2,2-trichloro-ethyl ester → (+)-spectinomycin dihydrochloride (21736-83-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) p-TsOH; 2.) Dowex-1 (OH-) / benzene / 1 h / 25 °C

2: 270 mg / H₂O / 0.5 h

3: PCC / benzene / 1 h / Heating

4: 60 mg / zinc dust / acetic acid / 30 h / 1.) refux, 1 h, benzene, 2.) glacial ac. acid, 30 h

5: 1.) 1N sodium methoxyde (pH 8); 2.) Dowex-50 (H+) / methanol / 0.25 h / 25 °C

6: 80 percent / 1.) bis(tri-n-butyltin)oxide, 2.)NBS / benzene / 25 °C / 1.) 1 h, 2.) 10 h

7: 90 percent / H₂ / palladium-on-charcoal / H₂O; propan-2-ol

With N-Bromosuccinimide; Dowex-1 (OH-); Dowex-50 (H+); hydrogen; sodium methylate; toluene-4-sulfonic acid; pyridinium chlorochromate; bis(tri-n-butyltin)oxide; zinc; palladium on activated charcoal; In methanol; water; acetic acid; isopropyl alcohol; benzene;

DOI:10.1139/v85-026

upstream raw materials:

N,N'-<(benzyloxy)carbonyl>spectinomycin

4-O-acetyl-N,N'-<(benzyloxy)carbonyl>-4(R)-dihydrospectinomycin

Carbonic acid (1R,2S,3R,4R,5S,6R)-2,4-bis-(benzyloxycarbonyl-methyl-amino)-6-((3aR,4S,6R,7aR)-2-methoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-3,5-bis-(2,2,2-trichloro-ethoxycarbonyloxy)-cyclohexyl ester 2,2,2-trichloro-ethyl ester

4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

Downstream raw materials:

[(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-5-((2S,3R,4S,6R)-3,4-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,4,6-trihydroxy-cyclohexyl]-methyl-carbamic acid benzyl ester

N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

N,N'-<(benzyloxy)carbonyl>-4(R)-dihydrospectinomycin

N,N'-<(benzyloxy)carbonyl>-4-(S)-dihydrospectinomycin

Refernces