(S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione

Base Information

Chemical Name:(S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione
CAS No.:166533-66-0
Molecular Formula:C₂₉H₃₉NO₆Si
Molecular Weight:525.717
Hs Code.:

(S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione

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Chemical Property of (S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione

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Technology Process of (S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione

There total 6 articles about (S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione 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:

: 527-69-5
2-furancarbonyl chloride

: 166533-65-9
(+)-N-<1-oxo-5-(tert-butyldimethylsilyl)oxy-6-methylhept-6-ene>-2-methyl-3-phenyl-4-oxazolidin-5-one

: 166533-66-0
(S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1016/0040-4039(95)01083-T

Reference yield:

: 130892-17-0
ethyl 6-methyl-5-oxo-6-heptenoate

: 166533-66-0
(S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / BH₃*SMe₂, (R)-diphenyl-2-pyrrolidino methanol oxazaborole / tetrahydrofuran / 18 h / -20 °C

2: 86 percent / imidazole / dimethylformamide / 4 h / 25 °C

3: NaOH / propan-2-ol / 5 h / Heating

4: (COCl)2, DMF / toluene; CH₂Cl₂ / 12 h / -10 - 25 °C

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, toluene, hexane, -78 deg C, 4 h

6: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 2 h, 2.) THF, 4 h

With 1H-imidazole; sodium hydroxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; (R)-diphenyl-2-pyrrolidino methanol oxazaborole; N,N-dimethyl-formamide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1016/0040-4020(96)00867-8

Reference yield:

: 166533-63-7
(S)-ethyl 5-hydroxy-6-methyl-6-heptenoate

: 166533-66-0
(S)-2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyl]-1-furan-2-yl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-propane-1,3-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / imidazole / dimethylformamide / 4 h / 25 °C

2: NaOH / propan-2-ol / 5 h / Heating

3: (COCl)2, DMF / toluene; CH₂Cl₂ / 12 h / -10 - 25 °C

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, toluene, hexane, -78 deg C, 4 h

5: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 2 h, 2.) THF, 4 h

With 1H-imidazole; sodium hydroxide; n-butyllithium; oxalyl dichloride; N,N-dimethyl-formamide; lithium hexamethyldisilazane; In dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1016/0040-4020(96)00867-8