(2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one

Base Information

Chemical Name:(2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one
CAS No.:251908-43-7
Molecular Formula:C₂₅H₃₇NO₄Si
Molecular Weight:443.659
Hs Code.:

Synonyms:(2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one

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Chemical Property of (2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one

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Technology Process of (2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one

There total 4 articles about (2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one 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%

: 251908-42-6
(2'E,4S,5'S)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-oxo-2'-heptenoyl]-oxazolidin-2-one

: 1730-25-2
allylmagnesium bromide

: 251908-43-7
(2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one

: 251908-44-8
(2'E,4S,5'S,7'S)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one

Guidance literature:: allylmagnesium bromide; With B-methoxy-bis(2-isocaranyl)borane; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 1.25h;

(2'E,4S,5'S)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-oxo-2'-heptenoyl]-oxazolidin-2-one; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

With water; dihydrogen peroxide; In tetrahydrofuran; methanol; diethyl ether; for 15h; Heating;
DOI:10.1002/(SICI)1521-3765(19991001)5:10<2850::AID-CHEM2850>3.0.CO;2-7

Reference yield:

: 251908-67-5
(S,E)‐3‐(but‐2‐enoyl)‐4‐(tert‐butyl)oxazolidin‐2‐one

: 251908-43-7
(2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

1.2: 82 percent / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3.1: toluene / 1 h / 170 °C

3.2: 68 percent / p-TsOH*H₂O / 0.25 h / 20 °C

4.1: B-methoxy-bis(4-isocaranyl)borane / tetrahydrofuran; diethyl ether / 1.25 h / -78 - 20 °C

4.2: tetrahydrofuran; diethyl ether / 1 h / -78 °C

4.3: H₂O₂; H₂O / tetrahydrofuran; diethyl ether; methanol / 15 h / Heating

With 2,6-dimethylpyridine; B-methoxy-bis(2-isocaranyl)borane; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Substitution / 1.2: Condensation / 2.1: Etherification / 3.1: Rearrangement / 3.2: Hydrolysis / 4.1: Substitution / 4.2: Addition / 4.3: Hydrolysis;
DOI:10.1002/(SICI)1521-3765(19991001)5:10<2850::AID-CHEM2850>3.0.CO;2-7

Reference yield:

: 251908-41-5
(2'S,3'R,4S,4'E)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-2'-ethenyl-3'-hydroxy-4'-pentenoyl]-oxazolidin-2-one

: 251908-43-7
(2'E,4S,5'S,7'R)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-hydroxy-2',9'-decanedienoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: toluene / 1 h / 170 °C

2.2: 68 percent / p-TsOH*H₂O / 0.25 h / 20 °C

3.1: B-methoxy-bis(4-isocaranyl)borane / tetrahydrofuran; diethyl ether / 1.25 h / -78 - 20 °C

3.2: tetrahydrofuran; diethyl ether / 1 h / -78 °C

3.3: H₂O₂; H₂O / tetrahydrofuran; diethyl ether; methanol / 15 h / Heating

With 2,6-dimethylpyridine; B-methoxy-bis(2-isocaranyl)borane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Etherification / 2.1: Rearrangement / 2.2: Hydrolysis / 3.1: Substitution / 3.2: Addition / 3.3: Hydrolysis;
DOI:10.1002/(SICI)1521-3765(19991001)5:10<2850::AID-CHEM2850>3.0.CO;2-7