[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

Base Information

• Chemical Name: [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester
• CAS No.: 541501-17-1
• Molecular Formula: C₃₀H₃₇BrO₅
• Molecular Weight: 557.525

Synonyms:[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

Chemical Property of [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

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Technology Process of [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

There total 15 articles about [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester 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: 95.0%

benzyl bromide (100-39-0) + C23H31BrO5 → [1'(2)R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester (541501-17-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In acetonitrile; at 20 ℃;

Reference yield:

(-)-(4aS,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone (155486-89-8) → [1'(2)R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester (541501-17-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -20 - 0 °C

1.2: tetrahydrofuran; hexane / 0.5 h / 0 °C

2.1: molecular sieves 4 Angstroem; benzyltrimethylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

2.2: 2.16 g / hydrazine; AcOH / ethanol / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: tetrahydrofuran; hexane / 2 h / -78 - 0 °C

4.1: 1.81 g / NaBH₃CN; ZnI₂ / CH₂Cl₂ / 4 h / 0 °C

5.1: thionyl chloride / 2.5 h / Heating

6.1: 66 mg / Raney Ni; hydrogen / tetrahydrofuran; H₂O / 16 h

7.1: hydrogen / Pd/C / ethanol / 8 h

8.1: 389 mg / Amberlyst 15 / CH₂Cl₂ / 72 h / 0 °C

9.1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

10.1: NBS / CH₂Cl₂ / 10 h / 20 °C

10.2: 45 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

11.1: 95 percent / K₂CO₃; n-Bu₄NI / acetonitrile / 20 °C

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; thionyl chloride; Amberlyst 15; 4 A molecular sieve; hydrogen; tetra-(n-butyl)ammonium iodide; trimethyl(benzyl)ammonium fluoride; nickel; sodium cyanoborohydride; potassium carbonate; zinc(II) iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetonitrile;

Reference yield:

[2R,4aS,6R,8aS]-4-(6-benzyloxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-ylmethyl)-3,5-dihydroxybenzoic acid methyl ester (541501-09-1) → [1'(2)R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester (541501-17-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen / Pd/C / ethanol / 8 h

2.1: 389 mg / Amberlyst 15 / CH₂Cl₂ / 72 h / 0 °C

3.1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

4.1: NBS / CH₂Cl₂ / 10 h / 20 °C

4.2: 45 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

5.1: 95 percent / K₂CO₃; n-Bu₄NI / acetonitrile / 20 °C

With 1H-imidazole; N-Bromosuccinimide; Amberlyst 15; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile;

upstream raw materials:

benzyl bromide

(-)-(4aS,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone

[2R,4aS,6R,8aS]-6-benzyloxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde

3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

Downstream raw materials:

[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-6'-hydroxy-7-cyano-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-ethenyl-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

stachybotrylactam

[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-formyl-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

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