(2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal

Base Information

Chemical Name:(2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal
CAS No.:147122-18-7
Molecular Formula:C₃₀H₄₁NO₅Si
Molecular Weight:523.745
Hs Code.:

Synonyms:(2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal

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Chemical Property of (2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal

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Technology Process of (2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal

There total 2 articles about (2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal 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:

: 147122-17-6
(S)-3-[(2S,4S,5S,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-2,4-dimethyl-heptanoyl]-4-isopropyl-oxazolidin-2-one

: 147122-18-7
(2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; at 25 ℃; for 16h; Yield given;
DOI:10.1021/jo00060a036

Reference yield:

: 147121-97-9
(2'S,4S,4'S,5'S,6'R)-3-<5'-<(tert-Butyldiphenylsilyl)oxy>-2',4'-dimethyl-6',7'-O-isopropylideneheptanoyl>-4-isopropyl-1,3-oxazolidin-2-one

: 147122-18-7
(2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / aq.HOAc / tetrahydrofuran / 3 h / Heating

2: NaIO₄ / H₂O; tetrahydrofuran / 16 h / 25 °C

With sodium periodate; acetic acid; In tetrahydrofuran; water;
DOI:10.1021/jo00060a036

Reference yield:

: 147122-18-7
(2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal

: (1'E,7'Z,9'E,11'E)-(3'S,5'S,6'S)-6-<8'-Bromo-6'-<(tert-butyldiphenylsilyl)oxy>-13'-hydroxy-1',3',5',11'-tetramethyltrideca-1',7',9',11'-tetraenyl>-2,2-dimethyl-1,3-dioxin-4-one

Guidance literature:: Multi-step reaction with 5 steps

1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 34 percent / DIBAL-H / CH₂Cl₂ / -50 to -10 deg C, then 16 h

3: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 30 min, 2) to 25 deg C over 1 h

4: 1) lithium hexamethyldisilazide / 1) THF, 0 deg C, 10 min, 2) THF, 0 deg C, 2 h

5: 86 percent / aq.TlOH / Pd(PPh₃)4 / tetrahydrofuran / 0.17 h / 25 °C

With TlOH; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00060a036