Punctaporonin D

Base Information

• Chemical Name: Punctaporonin D
• CAS No.: 102734-12-3
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354
• DSSTox Substance ID: DTXSID70908024
• Wikidata: Q77384660
• Metabolomics Workbench ID: 111961
• Mol file: 102734-12-3.mol

Synonyms:M 167906;M167906;punctaporonin D

Chemical Property of Punctaporonin D

Chemical Property:

• Vapor Pressure: 2.21E-07mmHg at 25°C
• Boiling Point: 381.3°Cat760mmHg
• Flash Point: 177.3°C
• PSA: 60.69000
• Density: 1.226g/cm³
• LogP: 1.47310
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 252.17254462
• Heavy Atom Count: 18
• Complexity: 416

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2C1(CCC3(C2(C=CC3O)CO)C)O)C
• Isomeric SMILES: C[C@]12CC[C@@]3([C@@H]([C@]1(C=C[C@@H]2O)CO)CC3(C)C)O

Technology Process of Punctaporonin D

There total 18 articles about Punctaporonin D 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:

(2aS,4aS,7aS,7bR)-1,2,2a,3,4,4a,7a,7b-octahydro-2a,7a-dihydroxy-2,2,4a-trimethyl-5H-cyclobutinden-5-one (106673-29-4) → punctaporonin D (102734-12-3)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ja00273a056

Reference yield:

(S)-Halos-Parish ketone (17553-86-5) → punctaporonin D (102734-12-3)

Guidance literature:

Multi-step reaction with 16 steps

1: lithium tri-tert-butoxyaluminum hydride

2: 95.5 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / Ambient temperature

3: 40 percent / 50percent NaH / dimethylsulfoxide / 1 h / Ambient temperature

4: H₂ / 10percent Pd-C / ethanol / 26 h / 760 Torr

5: 97 percent / LiAlH₄ / diethyl ether / 0.5 h / -30 °C

6: 1.) KH, 2.) n-BuLi / 1.) THF, 1.5 h, room temp., 2.) THF, hexane, -78 deg C, 2 h, -78 deg C -> room temp., 6 h

7: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / 0.33 h / Ambient temperature

8: 1.) 1 M BH₃*THF, 2.) 3 M NaOH, 40percent H₂O₂ / 1.) 2-methoxyethyl ether, room temp., 24 h, 2.) THF, water, 50 deg C, 1 h

9: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h

10: 348 mg / NaOCH₃ / methanol / 9.5 h / Heating

11: 36.8 percent / benzene / 9.5 h / Irradiation

12: 81.2 percent / tetra-n-butylammonium fluoride trihydrate / bis-(2-methoxy-ethyl) ether / 36 h / 55 °C / 2 Torr

13: 80.5 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

14: 1.) tetra-n-butylammonium fluoride, 2.) Pd(OAc)2 / 1.) THF, 30 min, 2.) CH₃CN, 33.5 h

15: 73 percent / 35percent HClO₄ / tetrahydrofuran / 70 h / Ambient temperature

16: 1.5 mg / diisobutylaluminum hydride / tetrahydrofuran / 3 h / 0 °C

With palladium diacetate; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; borane-THF; lithium tri(t-butoxy)aluminum hydride; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium methylate; potassium hydride; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; diethylene glycol dimethyl ether; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00244a025

Reference yield:

(1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one (16271-49-1) → punctaporonin D (102734-12-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 95.5 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / Ambient temperature

2: 40 percent / 50percent NaH / dimethylsulfoxide / 1 h / Ambient temperature

3: H₂ / 10percent Pd-C / ethanol / 26 h / 760 Torr

4: 97 percent / LiAlH₄ / diethyl ether / 0.5 h / -30 °C

5: 1.) KH, 2.) n-BuLi / 1.) THF, 1.5 h, room temp., 2.) THF, hexane, -78 deg C, 2 h, -78 deg C -> room temp., 6 h

6: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / 0.33 h / Ambient temperature

7: 1.) 1 M BH₃*THF, 2.) 3 M NaOH, 40percent H₂O₂ / 1.) 2-methoxyethyl ether, room temp., 24 h, 2.) THF, water, 50 deg C, 1 h

8: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h

9: 348 mg / NaOCH₃ / methanol / 9.5 h / Heating

10: 36.8 percent / benzene / 9.5 h / Irradiation

11: 81.2 percent / tetra-n-butylammonium fluoride trihydrate / bis-(2-methoxy-ethyl) ether / 36 h / 55 °C / 2 Torr

12: 80.5 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

13: 1.) tetra-n-butylammonium fluoride, 2.) Pd(OAc)2 / 1.) THF, 30 min, 2.) CH₃CN, 33.5 h

14: 73 percent / 35percent HClO₄ / tetrahydrofuran / 70 h / Ambient temperature

15: 1.5 mg / diisobutylaluminum hydride / tetrahydrofuran / 3 h / 0 °C

With palladium diacetate; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; borane-THF; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium methylate; potassium hydride; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; diethylene glycol dimethyl ether; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00244a025

upstream raw materials:

(2aS,4aS,7aS,7bR)-1,2,2a,3,4,4a,7a,7b-octahydro-2a,7a-dihydroxy-2,2,4a-trimethyl-5H-cyclobutinden-5-one

(2aS,4aS,5S,7bR)-decahydro-7a-(methoxymethoxy)-2,2,4a-trimethyl-2aH-cyclobutindene-2a,5-diol

(2aS,4aS,7aS,7bR)-decahydro-2a-hydroxy-7a-(methoxymethoxy)-2,2,4a-trimethyl-5H-cyclobutinden-5-one

(1S,3aS,7aS)-7,7a-dihydro-4-isobutyl-7a-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>-3a(6H)-indanmethanol