COUMERMYCIN A1

Base Information

• Chemical Name: COUMERMYCIN A1
• CAS No.: 4434-05-3
• Molecular Formula: C55H59N5O20
• Molecular Weight: 1110.19
• Mol file: 4434-05-3.mol

Synonyms:Notomycin;l)oxy)-4-hydroxy-8-methylcoumarin);notomycina1;Sugordomycin D-la;Coumermycin;COUMERMYCIN A1;coumamycin;coumermycins;Cumamycin;

Chemical Property of COUMERMYCIN A1

Chemical Property:

• Melting Point: 259°C (rough estimate)
• Refractive Index: 1.7210 (estimate)
• Boiling Point: 821.5°C (rough estimate)
• PKA: pKa 6.0±0.02(H2O ) (Uncertain)
• PSA: 354.89000
• Density: 1.1866 (rough estimate)
• LogP: 5.71790
• Solubility.: DMSO: 50 mg/mL, clear, faintly yellow

Purity/Quality:

97% ^*data from raw suppliers

Coumermycin A1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 470805
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Antibacterial.

Technology Process of COUMERMYCIN A1

There total 12 articles about COUMERMYCIN A1 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: 85.0%

3-methyl-1H-pyrrole-2,4-dicarboxylic acid (3780-41-4) + 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-(3-amino-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester (25936-59-8) → coumermycin A1 (4434-05-3)

Guidance literature:

With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)02487-5

Reference yield:

5-methyl-1H-pyrrole-2-carboxylic acid (3757-53-7) → coumermycin A1 (4434-05-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 88 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl / CH₂Cl₂

2.1: 83 percent / Bu₃P / CH₂Cl₂ / 72 h / 20 °C

3.1: 98 percent / trifluoroacetic acid / CH₂Cl₂; H₂O / 20 °C

4.1: 49 percent / diethyl azodicarboxylate; PPh₃ / CH₂Cl₂ / 20 °C

5.1: H₂ / Pd/C / tetrahydrofuran; methanol

6.1: aniline; NaNO₂; NaOAc / aq. HCl; methanol; tetrahydrofuran

6.2: Na₂S₂O₄; NaOAc / ethanol; H₂O; tetrahydrofuran

7.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide

With 4-methyl-morpholine; tributylphosphine; hydrogen; sodium acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; aniline; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium nitrite; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; hydrogenchloride; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Mitsunobu reaction;

DOI:10.1016/S0040-4039(02)02487-5

Reference yield:

ethyl 5-methyl-1H-pyrrole-2-carboxylate (3284-51-3) → coumermycin A1 (4434-05-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / LiOH / tetrahydrofuran; H₂O / 20 °C

2.1: 88 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl / CH₂Cl₂

3.1: 83 percent / Bu₃P / CH₂Cl₂ / 72 h / 20 °C

4.1: 98 percent / trifluoroacetic acid / CH₂Cl₂; H₂O / 20 °C

5.1: 49 percent / diethyl azodicarboxylate; PPh₃ / CH₂Cl₂ / 20 °C

6.1: H₂ / Pd/C / tetrahydrofuran; methanol

7.1: aniline; NaNO₂; NaOAc / aq. HCl; methanol; tetrahydrofuran

7.2: Na₂S₂O₄; NaOAc / ethanol; H₂O; tetrahydrofuran

8.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide

With 4-methyl-morpholine; lithium hydroxide; tributylphosphine; hydrogen; sodium acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; aniline; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium nitrite; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; hydrogenchloride; methanol; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Mitsunobu reaction;

DOI:10.1016/S0040-4039(02)02487-5

upstream raw materials:

3-methyl-1H-pyrrole-2,4-dicarboxylic acid

5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-(3-amino-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester

5-methyl-1H-pyrrole-2-carboxylic acid

ethyl 5-methyl-1H-pyrrole-2-carboxylate

Downstream raw materials:

5-{2-Hydroxy-4-[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyloxy)-tetrahydro-pyran-2-yloxy]-3-methyl-phenyl}-2-methyl-oxazole-4-carboxylic acid methyl ester