[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-(tert-butyldiphenylsilyloxy)-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-(tert-butyldiphenylsilyloxy)-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.: 541501-16-0
• Molecular Formula: C₃₉H₅₀O₅Si
• Molecular Weight: 626.909

Synonyms:[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-(tert-butyldiphenylsilyloxy)-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-(tert-butyldiphenylsilyloxy)-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-(tert-butyldiphenylsilyloxy)-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 13 articles about [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-(tert-butyldiphenylsilyloxy)-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: 96.0%

tert-butylchlorodiphenylsilane (58479-61-1) + [1'(2)R,2'R,4'aS,6'R,8'aS]-4,6'-dihydroxy-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 (541501-11-5) → [1'(2)R,2'R,4'aS,6'R,8'aS]-4-(tert-butyldiphenylsilyloxy)-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 (541501-16-0)

Guidance literature:

With 1H-imidazole; In dichloromethane; 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-(tert-butyldiphenylsilyloxy)-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 (541501-16-0)

Guidance literature:

Multi-step reaction with 10 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

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

Reference yield:

3,5-Bis-benzyloxy-4-((4aR,6R,8aS)-6-benzyloxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester (541501-08-0) → [1'(2)R,2'R,4'aS,6'R,8'aS]-4-(tert-butyldiphenylsilyloxy)-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 (541501-16-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 mg / Raney Ni; hydrogen / tetrahydrofuran; H₂O / 16 h

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

3: 389 mg / Amberlyst 15 / CH₂Cl₂ / 72 h / 0 °C

4: 96 percent / imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; Amberlyst 15; hydrogen; nickel; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water;

upstream raw materials:

tert-butylchlorodiphenylsilane

[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4,6'-dihydroxy-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

(-)-(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

Downstream raw materials:

stachybotrylactam

[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

[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-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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