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

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Chemical Name:(S)-3-[(2S,4S,5S,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-2,4-dimethyl-heptanoyl]-4-isopropyl-oxazolidin-2-one
CAS No.:147122-17-6
Molecular Formula:C₃₁H₄₅NO₆Si
Molecular Weight:555.787
Hs Code.:

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

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

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

There total 1 articles about (S)-3-[(2S,4S,5S,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-2,4-dimethyl-heptanoyl]-4-isopropyl-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: 99.0%

: 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

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

Guidance literature:: With acetic acid; In tetrahydrofuran; for 3h; Heating;
DOI:10.1021/jo00060a036

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

: 6-[(1E,7Z,9E,11E)-(3S,5S,6S)-13-Benzyloxymethoxy-8-bromo-6-(tert-butyl-diphenyl-silanyloxy)-1,3,5,11-tetramethyl-trideca-1,7,9,11-tetraenyl]-2,2-dimethyl-[1,3]dioxin-4-one

Guidance literature:: Multi-step reaction with 7 steps

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

2: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

3: 34 percent / DIBAL-H / CH₂Cl₂ / -50 to -10 deg C, then 16 h

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

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

6: 86 percent / aq.TlOH / Pd(PPh₃)4 / tetrahydrofuran / 0.17 h / 25 °C

7: 74 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / 25 °C

With sodium periodate; TlOH; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo00060a036

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

: C₇₂H₉₇BrO₈Si₃

Guidance literature:: Multi-step reaction with 8 steps

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

2: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

3: 34 percent / DIBAL-H / CH₂Cl₂ / -50 to -10 deg C, then 16 h

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

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

6: 88 percent / mol.-sieves 4 Angstroem / xylene / 1 h / 118 °C / other educt ratios, temperatures and reaction times

7: 1) tetra-n-propylammonium hydroxide / 1) THF, 2) Et₂O, 0 deg C

8: 65 percent / aq.TlOH / Pd(PPh₃)4 / tetrahydrofuran

With sodium periodate; TlOH; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; tetrapropylammonium hydroxide; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; xylene;
DOI:10.1021/jo00060a036