Pyripyropene A

Base Information

• Chemical Name: Pyripyropene A
• CAS No.: 147444-03-9
• Molecular Formula: C31H37 N O10
• Molecular Weight: 583.63
• European Community (EC) Number: 813-163-5
• ChEMBL ID: CHEMBL4518651
• DSSTox Substance ID: DTXSID601017602
• Metabolomics Workbench ID: 63467
• Nikkaji Number: J646.661C
• Pharos Ligand ID: UH4DVMH7R4JH,UH8GGXWFJP2H
• Wikidata: Q27133384
• Mol file: 147444-03-9.mol

Synonyms:pyripyropene A

Chemical Property of Pyripyropene A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 153-154℃
• Boiling Point: 690.753°C at 760 mmHg
• Flash Point: 371.554°C
• PSA: 151.46000
• Density: 1.339g/cm³
• LogP: 3.75530
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 583.24174638
• Heavy Atom Count: 42
• Complexity: 1230

Purity/Quality:

97% ^*data from raw suppliers

Pyripyropene A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1(C(CCC2(C1CC(C3(C2C(C4=C(O3)C=C(OC4=O)C5=CN=CC=C5)O)C)OC(=O)C)C)OC(=O)C)C
• Isomeric SMILES: CC(=O)OC[C@@]1([C@H](CC[C@]2([C@H]1C[C@@H]([C@@]3([C@@H]2[C@H](C4=C(O3)C=C(OC4=O)C5=CN=CC=C5)O)C)OC(=O)C)C)OC(=O)C)C
• Uses: Pyripyropene A exhibits insecticidal properties and a useful compound for developing agrichemicals.

Technology Process of Pyripyropene A

There total 34 articles about Pyripyropene 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: 96.0%

Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester (171925-86-3) → α-pyronemeroterpenoid pyripyropene A (147444-03-9)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol;

DOI:10.1021/jo00130a005

Reference yield: 79.0%

acetic anhydride (108-24-7) + 1,7,11-trideacetyl-pyripyropene A → α-pyronemeroterpenoid pyripyropene A (147444-03-9)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; for 2h; Ambient temperature;

Reference yield:

(4a'R,5'R,8a'S)-5'-(hydroxymethyl)-5',8a'-dimethylhexahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one (389103-83-7) → α-pyronemeroterpenoid pyripyropene A (147444-03-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 95 percent / Me₄NBH(OAc)3, AcOH / acetonitrile

2: NaH / tetrahydrofuran

3: 2 N HCl / tetrahydrofuran

4: 1.) KDA, TMSCl, Et₃N, 2.) BTAF, 4 Angstroem MS / 1.) THF, 2.) THF

5: 86 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / Heating

6: 72 percent / Pd(OAc)2, PPh₃, Et₃N / dimethylformamide

7: 1.) SeO₂, 2.) PCC, Celite, 3 Angstroem MS / 1.) dioxane, reflux, 2.) PhH

8: 99 percent / NaBH₄, CeCl₃*7H₂O / methanol

9: H₂ / Pd(OH)2 / methanol

10: NaH, PrSH / dimethylformamide

11: DMAP / pyridine

12: 100 percent / NaH, (COCl)2 / benzene / 1.) room temperature, 2 h, 2.) 2 h

13: 47 percent / trifluoroacetic acid / Heating

14: 96 percent / NaBH₄, CeCl₃*7H₂O / methanol

With hydrogenchloride; dmap; palladium diacetate; sodium tetrahydroborate; chloro-trimethyl-silane; selenium(IV) oxide; 2,6-di-tert-butyl-4-methylpyridine; cerium(III) chloride; oxalyl dichloride; 1-thiopropane; 3 Angstroem MS; 4 Angstroem MS; Celite; Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; hydrogen; sodium hydride; acetic acid; triethylamine; triphenylphosphine; pyridinium chlorochromate; tetramethylammonium triacetoxyborohydride; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; trifluoroacetic acid; benzene;

DOI:10.1021/jo00130a005

upstream raw materials:

acetic anhydride

Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

(4a'R,5'R,8a'S)-5'-(hydroxymethyl)-5',8a'-dimethylhexahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one

C₁₁H₁₄O₂C₂H₄OC₂H₆OH₂

Downstream raw materials:

7-O-p-cyanobenzoyl-1,11-O-(di-tert-butylsilylene)-1,7,11-trideacetylpyripyropene A

(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-((di-tert-butylfluorosilyl)oxy)-12-hydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate

(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate

(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-(((di-tert-butylfluorosilyl)oxy)methyl)-3,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12bdodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate