[(2S,2aR,4aR,7aR,7bS)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1,2,4a,5,7,7a-hexahydrocyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Base Information

• Chemical Name: [(2S,2aR,4aR,7aR,7bS)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1,2,4a,5,7,7a-hexahydrocyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
• CAS No.: 96684-80-9
• Molecular Formula: C₂₄H₂₉ClO₆
• Molecular Weight: 448.944
• DSSTox Substance ID: DTXSID60914396
• Wikidata: Q82885186
• Mol file: 96684-80-9.mol

Synonyms:armillaridin

Chemical Property of [(2S,2aR,4aR,7aR,7bS)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1,2,4a,5,7,7a-hexahydrocyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Chemical Property:

• Vapor Pressure: 1.98E-14mmHg at 25°C
• Boiling Point: 582.9°Cat760mmHg
• Flash Point: 306.3°C
• Density: 1.34g/cm³
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 448.1652663
• Heavy Atom Count: 31
• Complexity: 795

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=CC(=C1Cl)OC)O)C(=O)OC2CC3(C2(C(=CC4C3CC(C4)(C)C)C=O)O)C
• Isomeric SMILES: CC1=C(C(=CC(=C1Cl)OC)O)C(=O)O[C@H]2C[C@@]3([C@]2(C(=C[C@@H]4[C@H]3CC(C4)(C)C)C=O)O)C

Technology Process of [(2S,2aR,4aR,7aR,7bS)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1,2,4a,5,7,7a-hexahydrocyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

There total 25 articles about [(2S,2aR,4aR,7aR,7bS)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1,2,4a,5,7,7a-hexahydrocyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate 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: 63.0%

A52a (1297308-04-3) → armillaridin (96684-80-9)

Guidance literature:

With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; toluene-4-sulfonic acid; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201705308

Reference yield:

C32H40O4Si → armillaridin (96684-80-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / acetonitrile / 16 h / 70 °C / Inert atmosphere

2.1: 1,2-bis-(diphenylphosphino)ethane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / tetrahydrofuran / 35 °C / Inert atmosphere; Glovebox

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; aq. phosphate buffer; tert-butyl alcohol; acetone / pH 7 / Inert atmosphere

4.1: sodium periodate / tetrahydrofuran; water; aq. phosphate buffer / pH 7 / Inert atmosphere

5.1: N,N,N,N,N,N-hexamethylphosphoric triamide / dichloromethane / 3.5 h / pH 7 / Inert atmosphere; Sealed tube; Glovebox

6.1: dimethylsulfide; N-chloro-succinimide / toluene / 1.25 h / -20 - 0 °C / Inert atmosphere

6.2: 0.77 h / 0 - 20 °C / Inert atmosphere

7.1: sodium tris(acetoxy)borohydride; acetic acid / acetonitrile / 0 - 20 °C / Inert atmosphere

8.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 16 h / 45 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium periodate; N-chloro-succinimide; osmium(VIII) oxide; dimethylsulfide; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 2.1: |Tsuji-Wilkinson Decarbonylation / 6.1: |Corey-Kim Oxidation;

DOI:10.1002/anie.201705308

Reference yield:

(2E,6E)-ethyl 9-iodo-4,4-dimethyl-8-oxonona-2,6-dienoate → armillaridin (96684-80-9)

Guidance literature:

Multi-step reaction with 21 steps

1.1: benzene / 2 h / 85 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; hexane / 3 h / -78 °C / Inert atmosphere

3.1: manganese(IV) oxide / dichloromethane / 16 h / 23 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine; C₂₂H₂₄N₃O⁽¹⁺⁾*BF₄^(1-) / dichloromethane / 48 h / 40 °C / Inert atmosphere

5.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; dichloromethane / 3.5 h / 0 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / hexane; ethyl acetate / 1 h / 23 °C

7.1: barium(II) hydroxide / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere

7.2: 2 h / 23 °C / Inert atmosphere

8.1: dibromamine-T / acetonitrile; water / 0.25 h / Inert atmosphere

9.1: dmap; 1H-imidazole / dichloromethane / 12 h / 0 - 23 °C / Inert atmosphere

10.1: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 14 h / 75 °C / Inert atmosphere

11.1: lithium diisopropyl amide / hexane; diethyl ether / 1.08 h / -40 - 0 °C / Inert atmosphere

11.2: 2 h / -40 - 0 °C / Inert atmosphere

12.1: potassium carbonate / acetonitrile / 16 h / 70 °C / Inert atmosphere

13.1: 1,2-bis-(diphenylphosphino)ethane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / tetrahydrofuran / 35 °C / Inert atmosphere; Glovebox

14.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; aq. phosphate buffer; tert-butyl alcohol; acetone / pH 7 / Inert atmosphere

15.1: sodium periodate / tetrahydrofuran; water; aq. phosphate buffer / pH 7 / Inert atmosphere

16.1: N,N,N,N,N,N-hexamethylphosphoric triamide / dichloromethane / 3.5 h / pH 7 / Inert atmosphere; Sealed tube; Glovebox

17.1: dimethylsulfide; N-chloro-succinimide / toluene / 1.25 h / -20 - 0 °C / Inert atmosphere

17.2: 0.77 h / 0 - 20 °C / Inert atmosphere

18.1: sodium tris(acetoxy)borohydride; acetic acid / acetonitrile / 0 - 20 °C / Inert atmosphere

19.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 16 h / 45 °C / Inert atmosphere

20.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / Inert atmosphere

21.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; manganese(IV) oxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium periodate; N-chloro-succinimide; osmium(VIII) oxide; dimethylsulfide; palladium 10% on activated carbon; dibromamine-T; C₂₂H₂₄N₃O⁽¹⁺⁾*BF₄^(1-); 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; tetrabutyl ammonium fluoride; hydrogen; lithium carbonate; sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium tri-t-butoxyaluminum hydride; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; lithium bromide; barium(II) hydroxide; lithium diisopropyl amide; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 1.1: |Arbuzov Reaction / 13.1: |Tsuji-Wilkinson Decarbonylation / 17.1: |Corey-Kim Oxidation;

DOI:10.1002/anie.201705308

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