Pseudomonic acid C

Base Information

• Chemical Name: Pseudomonic acid C
• CAS No.: 71980-98-8
• Molecular Formula: C₂₆H₄₄O₈
• Molecular Weight: 484.631
• UNII: O6M926DF2R
• Nikkaji Number: J1.145.766E
• Metabolomics Workbench ID: 107931
• Mol file: 71980-98-8.mol

Synonyms:Pseudomonic acid C;71980-98-8;(+)-Pseudomonic acid C;UNII-O6M926DF2R;O6M926DF2R;Mupirocin calcium impurity B [EP];9-(((2E)-4-((2S,3R,4R,5S)-3,4-Dihydroxy-5-((2E,4R,5S)-5-hydroxy-4-methylhex-2-enyl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyl)oxy)nonanoic acid;L-TALO-NON-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-(5-hydroxy-4-methyl-2-hexen-1-yl)-3-methyl-, 8-carboxyoctyl ester, (2E)-;9-(((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-((4R,5S,E)-5-hydroxy-4-methylhex-2-en-1-yl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyl)oxy)nonanoic acid;SCHEMBL974341;PSEUDOMONIC ACID C [MI];KKMHFUKZHJOMJL-WZLBZGCNSA-N;AKOS040747315;MUPIROCIN IMPURITY B [EP IMPURITY];HY-133056;CS-0109970;MUPIROCIN CALCIUM IMPURITY B [EP IMPURITY];Q27285410;8-Carboxyoctyl (2E)-5,9-anhydro-2,3,4,8-tetradeoxy-8-[(2E,4R,5S)-5-hydroxy-4-methyl-2-hexen-1-yl]-3-methyl-L-talo-non-2-enonate;9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(E,4R,5S)-5-hydroxy-4-methylhex-2-enyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid

Chemical Property of Pseudomonic acid C

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 656.2°Cat760mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 210.3°C
• PSA: 133.52000
• Density: 1.125g/cm³
• LogP: 3.38130
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), methanol (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 17
• Exact Mass: 484.30361836
• Heavy Atom Count: 34
• Complexity: 659

Purity/Quality:

99% ^*data from raw suppliers

PseudomonicAcidC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C=CCC1COC(C(C1O)O)CC(=CC(=O)OCCCCCCCCC(=O)O)C)C(C)O
• Isomeric SMILES: C[C@H](/C=C/C[C@H]1CO[C@H]([C@@H]([C@@H]1O)O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)[C@H](C)O
• Uses: Pseudomonic Acid C, is the analogue of Pseudomonic Acid D (P839520) which is an antibiotic isolated from Pseudomonas fluorescens.

Technology Process of Pseudomonic acid C

There total 85 articles about Pseudomonic acid C 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: 77.0%

<2S-<2α(E),3β,4β,5α(2E,4S*,5R*)>>-9-<<3-methyl-1-oxo-4--2-butenyl>oxy>nonanoic acid methyl ester (72042-22-9) → pseudomonic acid C (71980-98-8)

Guidance literature:

With potassium hydroxide; sodium hydrogencarbonate; In tetrahydrofuran; ethanol; at 0 ℃; for 4.5h;

DOI:10.1021/jo00253a021

Reference yield:

<3aS-<3aα,4α,7aα,7α(2E,4S*,5R*)>>-3-oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolopyran-4-yl>-2-propanone (89726-74-9) → pseudomonic acid C (71980-98-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / NaH / tetrahydrofuran / 25 °C

2: 76 percent / HOAc, H₂O / 25 °C

3: 75 percent / KOH, NaHCO₃ / tetrahydrofuran; ethanol / 25 °C

With potassium hydroxide; water; sodium hydride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; ethanol;

DOI:10.1021/jo00383a046

Reference yield:

(3S,4R,5R)-2-Bromo-tetrahydro-pyran-3,4,5-triol (528869-25-2) → pseudomonic acid C (71980-98-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) Hydrogen, Et₃N 2.) MeONa / 2.) MeOH

2: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

3: 82 percent / xylene / 18 h / Heating

4: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

5: 86 percent / NaBH₄ / ethanol

6: 93 percent / imidazole / dimethylformamide

7: 94 percent / xylene / 7 h / Heating

8: 81 percent / tetrahydrofuran / -78 °C

9: 85 percent / N-Methylmorpholine-N-oxide, OsO₄

10: 93 percent / anhydr. CuSO₄, TsOH

11: 75 percent / tetrahydrofuran / 24 h / Ambient temperature

12: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

13: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature

14: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.

15: 50percent aq. AcOH / 72 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; molecular sieve; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

upstream raw materials:

Ethyl monate C

<2S-<2α(E),3β,4β,5α(2E,4S^*,5R^*)>>-9-<<3-methyl-1-oxo-4--2-butenyl>oxy>nonanoic acid methyl ester

9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester

methyl 9-hydroxynonanoate