trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene

Base Information

• Chemical Name: trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene
• CAS No.: 145332-91-8
• Molecular Formula: C₂₉H₄₆O₅Si₂
• Molecular Weight: 530.852

Synonyms:trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene

Chemical Property of trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene

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Technology Process of trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene

There total 2 articles about trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene 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: 90.0%

t-butyldimethylsiyl triflate (69739-34-0) + trans-1,2,3,4,4a,5,6,7,8,8aα-decahydro-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)-2(1H)-naphthalenone (145315-80-6) → trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene (145332-91-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00052a068

Reference yield:

2,3,4,4a,5,6,7,8-octahydro-1-<(dimethylphenylsilyl)methyl>-4a-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)-2(1H)-naphthalenone (145315-73-7) → trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene (145332-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / liq. NH₃, Li / tetrahydrofuran / 1) -78 deg C, 20 min, 2) -78 deg C to RT

2: 90 percent / NEt₃ / CH₂Cl₂ / 0 °C

With ammonia; lithium; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00052a068

Reference yield:

trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)naphthalene (145332-91-8) → {(4'aR,5'R,8'aR)-6'-(tert-Butyl-dimethyl-silanyloxy)-5'-[(dimethyl-phenyl-silanyl)-methyl]-4',4'a,5',8'-tetrahydro-3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'a-yl}-methanol (145332-92-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 8h; 0 deg C to RT;

DOI:10.1021/jo00052a068

upstream raw materials:

t-butyldimethylsiyl triflate

trans-1,2,3,4,4a,5,6,7,8,8aα-decahydro-1α-<(dimethylphenylsilyl)methyl>-4aβ-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)-2(1H)-naphthalenone

2,3,4,4a,5,6,7,8-octahydro-1-<(dimethylphenylsilyl)methyl>-4a-<(methyloxy)carbonyl>-6,6-(ethylenedioxy)-2(1H)-naphthalenone

Downstream raw materials:

{(4'aR,5'R,8'aR)-6'-(tert-Butyl-dimethyl-silanyloxy)-5'-[(dimethyl-phenyl-silanyl)-methyl]-4',4'a,5',8'-tetrahydro-3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'a-yl}-methanol

trans-1,4,4a,5,6,7,8,8aα-octahydro-2-(tert-butyldimethylsiloxy)-1α-<(dimethylphenylsilyl)methyl>-4αβ-<(methyloxy)methyl>-6,6-(ethylenedioxy)naphthalene

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