Motuporin

Base Information

• Chemical Name: Motuporin
• CAS No.: 141672-08-4
• Molecular Formula: C40H57 N5 O10
• Molecular Weight: 767.92
• DSSTox Substance ID: DTXSID701046048
• Wikidata: Q76280639
• Metabolomics Workbench ID: 149170
• ChEMBL ID: CHEMBL430145
• Mol file: 141672-08-4.mol

Synonyms:motuporin;nodularin V;nodularin-V

Chemical Property of Motuporin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1076°C at 760 mmHg
• Flash Point: 604.6°C
• Density: 1.161g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 767.41054303
• Heavy Atom Count: 55
• Complexity: 1480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nodularin
• Canonical SMILES: CC=C1C(=O)NC(C(C(=O)NC(C(=O)NC(C(C(=O)NC(CCC(=O)N1C)C(=O)O)C)C=CC(=CC(C)C(CC2=CC=CC=C2)OC)C)C(C)C)C)C(=O)O
• Isomeric SMILES: C/C=C\1/C(=O)N[C@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H]([C@@H](C(=O)N[C@H](CCC(=O)N1C)C(=O)O)C)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)/C)C(C)C)C)C(=O)O

Technology Process of Motuporin

There total 91 articles about Motuporin 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: 52.0%

dimethyl motuporine hydrate (170872-85-2) → (-)-motuporin (141672-08-4)

Guidance literature:

With barium dihydroxide; In methanol; water;

DOI:10.1021/jo9904617

Reference yield:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) → (-)-motuporin (141672-08-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / diethyl ether / 0 °C

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 1.5 h

3.1: 601 mg / BOP; DIPEA / CH₂Cl₂ / 44 h / 20 °C

4.1: TFA / CH₂Cl₂

5.1: 153 mg / HATU; collidine / dimethylformamide; CH₂Cl₂; toluene / 16 h / 0 - 20 °C

6.1: 95 percent / Zn; AcOH / 4 h / 20 °C

7.1: CH₂Cl₂ / 0.75 h / 20 °C

8.1: N-ethylmorpholine / CH₂Cl₂ / 0.08 h / 20 °C

8.2: 5.4 mg / HATU / CH₂Cl₂ / 24 h / 0 - 20 °C

9.1: 52 percent / Ba(OH)2 / methanol; H₂O / 24 h / 20 °C

With N-ethylmorpholine;; 2,3,5-trimethyl-pyridine; barium dihydroxide; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0206700

Reference yield:

(E)-(4S, 5S)-methyl-4-azido-6-hydroxy-5-methyl-hex-2-enoate (194149-69-4) → (-)-motuporin (141672-08-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 100 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: SnCl₂; MeOH / 6 h / 0 - 20 °C

3.1: aq. NaHCO₃ / dioxane / 14 h / 20 °C

4.1: O₃; pyridine / methanol / -78 °C

4.2: Me₂S / 4 h / 20 °C

5.1: 973 mg / CrCl₂ / tetrahydrofuran / 5 h / 20 °C

6.1: Cp₂Zr(H)Cl / tetrahydrofuran / 0.92 h / 20 - 50 °C

6.2: ZnCl₂ / tetrahydrofuran / 0.03 h / 20 °C

6.3: 84 percent / Pd(PPh₃)4 / 0.08 h / 20 °C

7.1: 100 percent / nBu₄NF / tetrahydrofuran / 1 h / 20 °C

8.1: 86 percent / PDC / dimethylformamide / 20 h / 20 °C

9.1: 16 mg / HATU; collidine / dimethylformamide; CH₂Cl₂; toluene / 16 h / 0 - 20 °C

10.1: 65 percent / TBAF*SiO₂ / tetrahydrofuran; dimethylformamide / 9 h / 20 °C

11.1: CH₂Cl₂ / 0.75 h / 20 °C

12.1: DIPEA / CH₂Cl₂ / 0.08 h / 20 °C

12.2: 12 percent / HATU / CH₂Cl₂ / 19 h / 0 - 20 °C

13.1: 52 percent / Ba(OH)2 / methanol; H₂O / 24 h / 20 °C

With pyridine; 1H-imidazole; chromium dichloride; 2,3,5-trimethyl-pyridine; methanol; barium dihydroxide; dipyridinium dichromate; Schwartz's reagent; tetrabutyl ammonium fluoride; silica gel; sodium hydrogencarbonate; ozone; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0206700

upstream raw materials:

dimethyl motuporine hydrate

Dimethylmotuporin

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid

(2R,3S)-3-methoxy-2-methyl-4-phenylbutanal

Downstream raw materials:

Dimethylmotuporin