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

Base Information

• Chemical Name: methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-tert-butyldimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate
• CAS No.: 1380425-59-1
• Molecular Formula: C₂₃H₃₃BrO₄Si
• Molecular Weight: 481.502

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

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

Chemical Property:

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

There total 2 articles about methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-tert-butyldimethylsiloxy-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: 53.0%

tert-butyl(cyclohex-1-en-1-yloxy)dimethylsilane (62791-22-4) + methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate (104093-34-7,608128-34-3) → methyl (4R,4aS,8aR)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1301224-16-7) + methyl (4S,4aR,8aS)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-63-7) + methyl (4S,4aS,8aS)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-53-5) + methyl (4R,4aR,8aR)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-52-4) + methyl (4S,4aR,8aR)-4-(p-bromophenyl)-8a-tert-butyldimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-86-4) + methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-tert-butyldimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-59-1) + methyl (4R,4aS,8aS)-4-(p-bromophenyl)-8a-tert-butyldimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-42-2)

Guidance literature:

methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate; 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; at 20 ℃; for 0.25h; Molecular sieve;

tert-butyl(cyclohex-1-en-1-yloxy)dimethylsilane; In dichloromethane; at -20 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/ejoc.201200056

Reference yield: 37.0%

tert-butyl(cyclohex-1-en-1-yloxy)dimethylsilane (62791-22-4) + methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate (104093-34-7,608128-34-3) → methyl (4R,4aS,8aR)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1301224-16-7) + methyl (4S,4aR,8aS)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-63-7) + methyl (4S,4aS,8aS)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-53-5) + methyl (4R,4aR,8aR)-4-(p-bromophenyl)-8a-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-52-4) + methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-tert-butyldimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-59-1)

Guidance literature:

methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate; 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; at 20 ℃; for 0.25h; Molecular sieve;

tert-butyl(cyclohex-1-en-1-yloxy)dimethylsilane; In dichloromethane; at -20 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/ejoc.201200056

Reference yield: 76.0%

methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-tert-butyldimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-59-1) → methyl (4R,4aR,8aS)-4-(p-bromophenyl)-8a-tert-butyldimethylsiloxy-4a,5,6,7,8,8a-hexahydro-4H-chromen-2-carboxylate (1380425-60-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at -20 ℃; for 10h; optical yield given as %ee;

DOI:10.1002/ejoc.201200056

upstream raw materials:

tert-butyl(cyclohex-1-en-1-yloxy)dimethylsilane

methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate

Downstream raw materials:

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

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

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

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

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