2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione

Base Information

Chemical Name:2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione
CAS No.:792922-89-5
Molecular Formula:C₃₇H₄₁NO₆Si
Molecular Weight:623.821
Hs Code.:

2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione

Synonyms:2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione

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Chemical Property of 2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione

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Technology Process of 2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione

There total 11 articles about 2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione 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: 21.0%

: 792922-88-4
4-benzyloxy-2-[2-(tert-butyldiphenylsilanyloxy)-1-(2-hydroxy-3,5-dimethoxy-4-methylphenyl)ethyl]pyrrolidin-3-ol

: 792922-89-5
2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione

Guidance literature:: With (NH₄)3Ce(NO₃)6; In water; acetonitrile; at 25 ℃; for 0.0833333h;
DOI:10.1021/jo048924i

Reference yield:

: 19676-67-6
2,4-dimethoxy-3-methylphenol

: 792922-89-5
2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

1.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

2.2: 86 percent / tetrahydrofuran; hexane / 0 - 25 °C

3.1: 89 percent / Et₃N; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

4.1: SmI₂; n-Bu₃SnCl / Pd(PPh₃)4 / tetrahydrofuran / 12 h / 25 °C

4.2: 1.22 g / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

5.1: O₃ / methanol / 0.5 h / -78 °C

5.2: 62 percent / NaBH₄ / methanol / 1 h / 0 °C

6.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

7.1: 79 percent / trifluoroacetic acid / CH₂Cl₂ / 0.17 h / 25 °C

8.1: 21 percent / (NH₄)3Ce(NO₃)6 / acetonitrile; H₂O / 0.08 h / 25 °C

With dmap; n-butyllithium; samarium diiodide; (NH₄)3Ce(NO₃)6; tributyltin chloride; sodium hydride; ozone; triethylamine; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo048924i

Reference yield:

: 7149-92-0
2,4-dimethoxy-3-methylbenzaldehyde

: 792922-89-5
2-benzyloxy-8-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-6-methoxy-5-methyl-2,3,8,8a-tetrahydro-1H-3a-azacyclopenta[a]-indene-4,7-dione

Guidance literature:: Multi-step reaction with 9 steps

1.1: m-CPBA / CH₂Cl₂ / 3 h / 0 °C

1.2: 87 percent / KOH / methanol / 1 h / 0 °C

2.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

2.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

3.2: 86 percent / tetrahydrofuran; hexane / 0 - 25 °C

4.1: 89 percent / Et₃N; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

5.1: SmI₂; n-Bu₃SnCl / Pd(PPh₃)4 / tetrahydrofuran / 12 h / 25 °C

5.2: 1.22 g / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

6.1: O₃ / methanol / 0.5 h / -78 °C

6.2: 62 percent / NaBH₄ / methanol / 1 h / 0 °C

7.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

8.1: 79 percent / trifluoroacetic acid / CH₂Cl₂ / 0.17 h / 25 °C

9.1: 21 percent / (NH₄)3Ce(NO₃)6 / acetonitrile; H₂O / 0.08 h / 25 °C

With dmap; n-butyllithium; samarium diiodide; (NH₄)3Ce(NO₃)6; tributyltin chloride; sodium hydride; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Baeyer-Villiger oxidation;
DOI:10.1021/jo048924i