Strongylin A

Base Information

• Chemical Name: Strongylin A
• CAS No.: 136978-48-8
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• Nikkaji Number: J3.204.686J
• Wikidata: Q27135133
• Metabolomics Workbench ID: 138831
• ChEMBL ID: CHEMBL490779
• Mol file: 136978-48-8.mol

Synonyms:strongylin A

Chemical Property of Strongylin A

Chemical Property:

• Vapor Pressure: 1.88E-09mmHg at 25°C
• Boiling Point: 469.9°Cat760mmHg
• PKA: 10.15±0.70(Predicted)
• Flash Point: 238°C
• PSA: 38.69000
• Density: 1.12g/cm³
• LogP: 5.33700
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 344.23514488
• Heavy Atom Count: 25
• Complexity: 517

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(CCCC23C1(CC4=C(C=CC(=C4O3)O)OC)C)(C)C
• Isomeric SMILES: C[C@H]1CC[C@@H]2[C@]3([C@@]1(CC4=C(C=CC(=C4O3)O)OC)C)CCCC2(C)C

Technology Process of Strongylin A

There total 11 articles about Strongylin 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: 84.0%

3-{[(1R,2S,4aS,8aS)-5-hydroxy-1,2,4a,5-tetramethyldecahydro-naphthalen-1-yl]methyl}-4-methoxybenzene-1,2-diol → (4aS,7S,7aR,13aS)-9-methoxy-4,4,7,7a-tetramethyl-1,2,3,4,4a,5,6,7,7a,8-decahydrobenzo[d]xanthen-12-ol (136978-48-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 0 ℃; for 3h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201300438

Reference yield:

[(4a'S,5'R,6'S,8a'S)-5',6',8a'-trimethyloctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methanol → (4aS,7S,7aR,13aS)-9-methoxy-4,4,7,7a-tetramethyl-1,2,3,4,4a,5,6,7,7a,8-decahydrobenzo[d]xanthen-12-ol (136978-48-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydrogen; palladium on activated charcoal / methanol

2.1: n-butyllithium / tetrahydrofuran; pentane / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

3.2: -78 - -65 °C / Inert atmosphere

3.3: -65 °C / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 5 h / Inert atmosphere; Reflux

5.1: hydrogenchloride / ethanol; water / 0 °C / Reflux

6.1: tetrahydrofuran; diethyl ether / 1 h / 20 °C / Inert atmosphere

6.2: 0 °C

7.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / -78 - 0 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; 2,2'-azobis(isobutyronitrile); palladium on activated charcoal; boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; pentane; benzene;

DOI:10.1002/ejoc.201300438

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) → (4aS,7S,7aR,13aS)-9-methoxy-4,4,7,7a-tetramethyl-1,2,3,4,4a,5,6,7,7a,8-decahydrobenzo[d]xanthen-12-ol (136978-48-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: potassium tert-butylate / benzene / 2 h / Reflux; Inert atmosphere

2.2: 0 °C / Inert atmosphere; Reflux

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

4.1: hydrogen; Crabtree's catalyst / dichloromethane / 1 h / 20 °C / 760.05 Torr

5.1: hydrogen; palladium on activated charcoal / methanol

6.1: n-butyllithium / tetrahydrofuran; pentane / 0 °C / Inert atmosphere

6.2: 0 - 20 °C / Inert atmosphere

7.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

7.2: -78 - -65 °C / Inert atmosphere

7.3: -65 °C / Inert atmosphere

8.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 5 h / Inert atmosphere; Reflux

9.1: hydrogenchloride / ethanol; water / 0 °C / Reflux

10.1: tetrahydrofuran; diethyl ether / 1 h / 20 °C / Inert atmosphere

10.2: 0 °C

11.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / -78 - 0 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; n-butyllithium; Crabtree's catalyst; 2,2'-azobis(isobutyronitrile); palladium on activated charcoal; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; pentane; benzene; 2.2: |Wittig Olefination;

DOI:10.1002/ejoc.201300438

upstream raw materials:

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

Refernces