methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate

Base Information

Chemical Name:methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate
CAS No.:186193-13-5
Molecular Formula:C₂₅H₃₂O₄Si
Molecular Weight:424.612
Hs Code.:

Synonyms:methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate

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Chemical Property of methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate

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Technology Process of methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate

There total 11 articles about methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate 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:

: 556834-69-6
methyl 5-(tert-butyldiphenylsilyloxy)-6-methyl-7-phenylsulfinyl-(E,5S,6S)-2-heptenoate

: 186193-13-5
methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate

Guidance literature:: methyl 5-(tert-butyldiphenylsilyloxy)-6-methyl-7-phenylsulfinyl-(E,5S,6S)-2-heptenoate; With triethylamine; trifluoroacetic anhydride; In acetonitrile; at 20 ℃; for 0.5h;

With sodium hydrogencarbonate; In water; acetonitrile; at 0 - 20 ℃;
DOI:10.1021/jo026802p

Reference yield:

: 556834-58-3
methyl 4-methyl-5-phenylsulfanyl-(Z,4S)-2-pentenoate

: 186193-13-5
methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / NaIO₄ / methanol; H₂O / 0 - 20 °C

2.1: 80 percent / N-bromosuccinimide; water / toluene / 3 h / 20 °C

3.1: 82 percent / tributyltin hydride; N,N'-azobis(isobutyronitrile) / benzene / 3 h / 80 °C

4.1: 70 percent / imidazole / CH₂Cl₂ / 24 h / 20 °C

5.1: DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

6.1: 0.70 g / benzene / 0.5 h / 20 °C

7.1: trifluoroacetic anhydride; triethylamine / acetonitrile / 0.5 h / 20 °C

7.2: NaHCO₃ / acetonitrile; H₂O / 0 - 20 °C

With 1H-imidazole; sodium periodate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triethylamine; trifluoroacetic anhydride; In methanol; dichloromethane; water; toluene; acetonitrile; benzene; 7.1: Pummerer reaction;
DOI:10.1021/jo026802p

Reference yield:

: 556834-61-8
methyl 4-methyl-5-phenylsulfinyl-(Z,4S)-2-pentenoate

: 186193-13-5
methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 80 percent / N-bromosuccinimide; water / toluene / 3 h / 20 °C

2.1: 82 percent / tributyltin hydride; N,N'-azobis(isobutyronitrile) / benzene / 3 h / 80 °C

3.1: 70 percent / imidazole / CH₂Cl₂ / 24 h / 20 °C

4.1: DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

5.1: 0.70 g / benzene / 0.5 h / 20 °C

6.1: trifluoroacetic anhydride; triethylamine / acetonitrile / 0.5 h / 20 °C

6.2: NaHCO₃ / acetonitrile; H₂O / 0 - 20 °C

With 1H-imidazole; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triethylamine; trifluoroacetic anhydride; In dichloromethane; toluene; acetonitrile; benzene; 6.1: Pummerer reaction;
DOI:10.1021/jo026802p