(S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

Base Information

Chemical Name:(S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one
CAS No.:151058-19-4
Molecular Formula:C₂₃H₃₇NO₅Si
Molecular Weight:435.636
Hs Code.:

Synonyms:(S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

There total 1 articles about (S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-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: 80.0%

: 97826-89-6
(2R)-3-(tert-butyldimethylsilyloxy)-2-methylpropanal

: 131685-53-5,101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: 151058-19-4
(S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane;
DOI:10.1021/jo00074a005

Reference yield:

: 151058-19-4
(S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

: C₃₆H₆₀O₅Si

Guidance literature:: Multi-step reaction with 14 steps

1.1: 95 percent / LiBH₄ / tetrahydrofuran; methanol / 0 °C

2.1: 87 percent / PPTS / CH₂Cl₂ / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / 0 °C

4.1: TBAF / tetrahydrofuran / 20 °C

5.1: (COCl)2; DMSO / CH₂Cl₂ / 1 h / -78 °C

5.2: Et₃N / tetrahydrofuran; CH₂Cl₂ / 0.17 h / -78 °C

5.3: 88 percent / NaBO₃*4H₂O; aq. NaHCO₃ / 10 h / 20 °C

6.1: 72 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

7.1: 66 percent / Et₃N / CH₂Cl₂ / 20 °C

8.1: DDQ; H₂O / CH₂Cl₂ / 20 °C

8.2: LiAlH₄; AlCl₃ / diethyl ether / 20 °C

9.1: 99 percent / PPTS / CH₂Cl₂ / 20 °C

10.1: 99 percent / DDQ; H₂O / CH₂Cl₂ / 20 °C

11.1: 45 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

12.1: 66 percent / K₃Fe(CN)6; K₂CO₃; (DHQ)2PYR / K₂OsO₄*H₂O / 2-methyl-propan-2-ol; H₂O / 0 °C

13.1: aq. NaIO₄ / tetrahydrofuran; methanol / 20 °C

14.1: tetrahydrofuran; methanol / 20 °C

With 2,6-dimethylpyridine; sodium periodate; lithium borohydride; oxalyl dichloride; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); 4 A molecular sieve; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); potassium osmate(VI); In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 5.1: Swern oxidation / 12.1: Sharpless's dihydroxylation reaction;
DOI:10.1016/j.tetlet.2006.11.079

Reference yield:

: 151058-19-4
(S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

: 1026707-16-3
C₃₂H₅₆O₆Si

Guidance literature:: Multi-step reaction with 12 steps

1.1: 95 percent / LiBH₄ / tetrahydrofuran; methanol / 0 °C

2.1: 87 percent / PPTS / CH₂Cl₂ / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / 0 °C

4.1: TBAF / tetrahydrofuran / 20 °C

5.1: (COCl)2; DMSO / CH₂Cl₂ / 1 h / -78 °C

5.2: Et₃N / tetrahydrofuran; CH₂Cl₂ / 0.17 h / -78 °C

5.3: 88 percent / NaBO₃*4H₂O; aq. NaHCO₃ / 10 h / 20 °C

6.1: 72 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

7.1: 66 percent / Et₃N / CH₂Cl₂ / 20 °C

8.1: DDQ; H₂O / CH₂Cl₂ / 20 °C

8.2: LiAlH₄; AlCl₃ / diethyl ether / 20 °C

9.1: 99 percent / PPTS / CH₂Cl₂ / 20 °C

10.1: 99 percent / DDQ; H₂O / CH₂Cl₂ / 20 °C

11.1: 45 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

12.1: 66 percent / K₃Fe(CN)6; K₂CO₃; (DHQ)2PYR / K₂OsO₄*H₂O / 2-methyl-propan-2-ol; H₂O / 0 °C

With 2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); 4 A molecular sieve; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); potassium osmate(VI); In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 5.1: Swern oxidation / 12.1: Sharpless's dihydroxylation reaction;
DOI:10.1016/j.tetlet.2006.11.079