Albocycline

Base Information

• Chemical Name: Albocycline
• CAS No.: 25129-91-3
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.418
• European Community (EC) Number: 803-490-1
• DSSTox Substance ID: DTXSID601113147
• Wikidata: Q76386791
• ChEMBL ID: CHEMBL4128170
• Mol file: 25129-91-3.mol

Synonyms:albocycline

Chemical Property of Albocycline

Chemical Property:

• Vapor Pressure: 1.25E-10mmHg at 25°C
• Boiling Point: 465.7°C at 760 mmHg
• Flash Point: 161.2°C
• PSA: 55.76000
• Density: 1.04g/cm³
• LogP: 3.17270
• Storage Temp.: ?20°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 308.19875937
• Heavy Atom Count: 22
• Complexity: 464

Purity/Quality:

95% ^*data from raw suppliers

Albocycline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC=C(C(C=CC(C=CC(=O)OC1C)(C)O)OC)C
• Isomeric SMILES: C[C@H]1CC/C=C(/[C@H](/C=C/[C@@](/C=C/C(=O)O[C@@H]1C)(C)O)OC)\C
• Uses: Albocycline is an antibiotic with selectivity mainly against staphylococci.

Technology Process of Albocycline

There total 35 articles about Albocycline 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: 87.0%

(3E,6E,9E)-(5R,8S,13S,14R)-8-Methoxy-5,9,13,14-tetramethyl-5-(tetrahydro-pyran-2-yloxy)-oxacyclotetradeca-3,6,9-trien-2-one (87518-68-1,87583-24-2) → (-)-albocycline (25129-91-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(01)90315-1

Reference yield:

(2R,3S)-4-((tert-butyldimethylsilyl)oxy)-3-methylbutan-2-ol (114972-47-3) → (-)-albocycline (25129-91-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 72 percent / diisopropylethyl amine / CH₂Cl₂ / Ambient temperature

2: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

3: 92 percent / CBr₄/PPh₃ / CH₂Cl₂ / 1 h / -40 °C

4: 80 percent / tetrabutylammonium bromide / dimethylformamide / 8 h / 40 °C

5: 1) butyllithium, HMPA, / 1) THF, hexane, -40 deg C, 90 min, -65 deg C, 10 min, 2) THF, -65 deg C - -10 deg C, 2.5 h

6: 87 percent / Na₂HPO₄, 6percent Na-amalgam / methanol / 2 h / Ambient temperature

7: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

8: 90 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / -60 °C

10: 98 percent / 1 M aq. LiOH / tetrahydrofuran; H₂O / Ambient temperature

11: 68 percent / H₂ / Pd(OH)2/C / hexane; ethyl acetate / 0.75 h / Ambient temperature

12: 82 percent / DCC, DMAP, DMAP*trifluoroacetate / ethanol; CHCl₃ / 10 h / Heating

13: 87 percent / pyridinium p-toluenesulfonate / methanol / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; 4-N,N-dimethylaminopyridine trifluoroacetate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90315-1

Reference yield:

(2S,3S)-4-[(tert-butyldimethylsilyl)oxy]-3-methylbutane-1,2-diol (114972-45-1) → (-)-albocycline (25129-91-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 92 percent / pyridine / -20 °C

2: 84 percent / LiB(Et)3H / tetrahydrofuran / 0.5 h / 0 °C

3: 72 percent / diisopropylethyl amine / CH₂Cl₂ / Ambient temperature

4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

5: 92 percent / CBr₄/PPh₃ / CH₂Cl₂ / 1 h / -40 °C

6: 80 percent / tetrabutylammonium bromide / dimethylformamide / 8 h / 40 °C

7: 1) butyllithium, HMPA, / 1) THF, hexane, -40 deg C, 90 min, -65 deg C, 10 min, 2) THF, -65 deg C - -10 deg C, 2.5 h

8: 87 percent / Na₂HPO₄, 6percent Na-amalgam / methanol / 2 h / Ambient temperature

9: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

10: 90 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / -60 °C

12: 98 percent / 1 M aq. LiOH / tetrahydrofuran; H₂O / Ambient temperature

13: 68 percent / H₂ / Pd(OH)2/C / hexane; ethyl acetate / 0.75 h / Ambient temperature

14: 82 percent / DCC, DMAP, DMAP*trifluoroacetate / ethanol; CHCl₃ / 10 h / Heating

15: 87 percent / pyridinium p-toluenesulfonate / methanol / 0 - 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; pyridinium p-toluenesulfonate; lithium triethylborohydride; dimethyl sulfoxide; 4-N,N-dimethylaminopyridine trifluoroacetate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90315-1

upstream raw materials:

(3E,6E,9E)-(5R,8S,13S,14R)-8-Methoxy-5,9,13,14-tetramethyl-5-(tetrahydro-pyran-2-yloxy)-oxacyclotetradeca-3,6,9-trien-2-one

(2R,3S)-4-((tert-butyldimethylsilyl)oxy)-3-methylbutan-2-ol

(2S,3S)-4-[(tert-butyldimethylsilyl)oxy]-3-methylbutane-1,2-diol

((1R,2R)-3-Bromo-1,2-dimethyl-propoxymethoxymethyl)-benzene