(3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate

Base Information

Chemical Name:(3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate
CAS No.:1357173-24-0
Molecular Formula:C₂₈H₃₉ClO₅Si
Molecular Weight:519.153
Hs Code.:

Synonyms:(3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate

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Chemical Property of (3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate

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Technology Process of (3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate

There total 5 articles about (3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate 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: 64.0%

: 1357173-16-0
dimethyl 2-(but-2-ynyl)-2-((1Z,3E)-4-(4-chlorophenyl)-2-(triisopropylsilyloxy)buta-1,3-dienyl)malonate

: 1357173-24-0
(3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate

Guidance literature:: With (R)-DTBM-SEGPHOS(AuCl)2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; In dichloromethane; at 20 ℃; for 16h; optical yield given as %ee; stereoselective reaction; Molecular sieve;
DOI:10.1021/ja210388g

Reference yield:

: 634906-78-8
(E)-1-bromo-4-(4-chlorophenyl)but-3-en-2-one

: 1357173-24-0
(3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

3.1: (R)-DTBM-SEGPHOS(AuCl)2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 16 h / 20 °C / Molecular sieve

With (R)-DTBM-SEGPHOS(AuCl)2; sodium hydride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; triethylamine; In tetrahydrofuran; dichloromethane; mineral oil;
DOI:10.1021/ja210388g

Reference yield:

: 1357173-66-0
(E)-dimethyl 2-(but-2-ynyl)-2-(4-(4-chlorophenyl)-2-oxobut-3-enyl)malonate

: 1357173-24-0
(3aS,4R,6aR)-dimethyl 4-(4-chlorophenyl)-3a-methyl-6-(triisopropylsilyloxy)-3a,4-dihydropentalene-1,1(6aH)-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

2: (R)-DTBM-SEGPHOS(AuCl)2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 16 h / 20 °C / Molecular sieve

With (R)-DTBM-SEGPHOS(AuCl)2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; triethylamine; In dichloromethane;
DOI:10.1021/ja210388g