Monic acid A

Base Information

• Chemical Name: Monic acid A
• CAS No.: 66262-68-8
• Molecular Formula: C₁₇H₂₈O₇
• Molecular Weight: 344.405
• UNII: TYE9LL9U8V
• Nikkaji Number: J1.292.895E
• Mol file: 66262-68-8.mol

Synonyms:monic acid A

Chemical Property of Monic acid A

Chemical Property:

• Vapor Pressure: 3.48E-15mmHg at 25°C
• Melting Point: 132-136°C
• Boiling Point: 566.3°Cat760mmHg
• PKA: 5.05±0.33(Predicted)
• Flash Point: 202.6°C
• PSA: 119.75000
• Density: 1.27g/cm³
• LogP: 0.31860
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Ethanol, Methanol
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 344.18350323
• Heavy Atom Count: 24
• Complexity: 478

Purity/Quality:

99% ^*data from raw suppliers

MonicAcidA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1C(O1)CC2COC(C(C2O)O)CC(=CC(=O)O)C)C(C)O
• Isomeric SMILES: C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)O)/C)[C@H](C)O
• Uses: Monic Acid A is the major metabolite of the antibiotic Mupirocin (M794000). Monic Acid A is also used in the preparation of cereal herbicide and mycoplasma inhibitors.

Technology Process of Monic acid A

There total 1 articles about Monic acid A 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:

→ Monic Acid A (66262-68-8,66290-01-5,70470-39-2)

Guidance literature:

Pseudomonic Saeure, Trimethylorthoformat;

Reference yield:

monic acid A (66262-68-8,66290-01-5,70470-39-2) → 2-(2-Bromo-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide (163913-93-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) i-BuOCOCl, NEt₃ / 1.) THF, 0 deg C, 30 min; 2.) CH₂Cl₂, RT, 1 h

2: NEt₃ / 4-dimethylaminopyridine / tetrahydrofuran / 2 h / Ambient temperature

3: 66 percent / 10 mol percent i-Pr₂NH, t-BuLi / 10 mol percent 4-dimethylaminopyridine / tetrahydrofuran / 2 h / Ambient temperature

With tert.-butyl lithium; triethylamine; diisopropylamine; isobutyl chloroformate; dmap; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73095-4

Reference yield:

monic acid A (66262-68-8,66290-01-5,70470-39-2) → 2-(2-Bromo-5-methoxy-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide (163913-94-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) i-BuOCOCl, NEt₃ / 1.) THF, 0 deg C, 30 min; 2.) CH₂Cl₂, RT, 1 h

2: NEt₃ / 4-dimethylaminopyridine / tetrahydrofuran / 2 h / Ambient temperature

3: 58 percent / 10 mol percent i-Pr₂NH, t-BuLi, 50 mol percent LiI / tetrahydrofuran

With tert.-butyl lithium; triethylamine; diisopropylamine; lithium iodide; isobutyl chloroformate; dmap; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73095-4

Downstream raw materials:

2-((E)-3-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-2-methyl-propenyl)-oxazole-5-carbaldehyde

(2S,3R,4R,5S)-5-[(2S,3S)-3-((1S,2S)-2-Hydroxy-1-methyl-propyl)-oxiranylmethyl]-2-[(E)-2-methyl-3-(5-phenylsulfanyl-oxazol-2-yl)-allyl]-tetrahydro-pyran-3,4-diol

((E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-3-methyl-but-2-enoylamino)-acetic acid phenyl ester

((E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-3-methyl-but-2-enoylamino)-thioacetic acid S-phenyl ester