methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

Base Information

Chemical Name:methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate
CAS No.:1380425-38-6
Molecular Formula:C₂₀H₂₇BrO₄Si
Molecular Weight:439.421
Hs Code.:

Synonyms:methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

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Chemical Property of methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

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Technology Process of methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

There total 3 articles about methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate 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: 62.0%

: 6651-36-1
1-(Trimethylsilyloxy)cyclohexene

: 104093-34-7,608128-34-3
methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate

: methyl (4R,4aR,8aR)-8a-hydroxy-4-phenyl-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

: 1380425-47-7
methyl (4R,4aR,8aR)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

: 1380425-38-6
methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

Guidance literature:: methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate; With 1,1,1,3',3',3'-hexafluoro-propanol; 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine; scandium tris(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; for 0.25h; Molecular sieve;

1-(Trimethylsilyloxy)cyclohexene; In dichloromethane; at -20 ℃; for 24h; optical yield given as %ee; enantioselective reaction;
DOI:10.1002/ejoc.201200056

Reference yield: 10.0%

: 1380425-47-7
methyl (4R,4aR,8aR)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

: 1380425-52-4
methyl (4R,4aR,8aR)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

: 1380425-38-6
methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

: 1380425-43-3
methyl (4R,4aS,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

Guidance literature:: With scandium tris(trifluoromethanesulfonate); at 20 ℃; for 18h; optical yield given as %ee; Molecular sieve;
DOI:10.1002/ejoc.201200056

Reference yield:

: 6651-36-1
1-(Trimethylsilyloxy)cyclohexene

: 1380425-52-4
methyl (4R,4aR,8aR)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

: 1380425-38-6
methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

: 1380425-43-3
methyl (4R,4aS,8aS)-4-(p-bromophenyl)-8a-trimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,6-bis[(4R)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-pyridine; 1,1,1,3',3',3'-hexafluoro-propanol; scandium tris(trifluoromethanesulfonate) / dichloromethane / 0.25 h / 20 °C / Molecular sieve

1.2: 24 h / -20 °C

2.1: scandium tris(trifluoromethanesulfonate) / 18 h / 20 °C / Molecular sieve

With 2,6-bis[(4R)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-pyridine; 1,1,1,3',3',3'-hexafluoro-propanol; scandium tris(trifluoromethanesulfonate); In dichloromethane;
DOI:10.1002/ejoc.201200056