(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one

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Chemical Name:(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one
CAS No.:154919-93-4
Molecular Formula:C₂₃H₃₇NO₅Si
Molecular Weight:435.636
Hs Code.:
Mol file:154919-93-4.mol

Synonyms:(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one Edit

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Technology Process of (S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one

There total 2 articles about (S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-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: 95.0%

: 87184-81-4
4-(tert-butyldimethylsilanyloxy)butanal

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

: 154919-93-4
(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine;
DOI:10.1021/ol026942l

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 154919-93-4
(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / pyridinium sulfur trioxide

With sulfur trioxide pyridine complex; 3: Evans syn-aldol condensation;
DOI:10.1021/jm0204136

Reference yield:

: 154919-93-4
(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one

: (2R)-2-{(4R,5S,6R)-6-[3-(tert-butyldimethylsilanyloxy)propyl]-2,2,5-trimethyl[1,3]dioxan-4-yl}propanoic acid, 2,6-dimethylphenyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / lithium borohydride / methanol; tetrahydrofuran / 2.33 h / 0 - 20 °C

2.1: 72 percent / pyridinium p-toluenesulfonate / benzene / 15 h / Heating

3.1: diisobutylaluminum hydride / tetrahydrofuran; CH₂Cl₂ / 1 h / 0 °C

4.1: pyridinium sulfur trioxide; diisopropylethylamine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

5.1: LDA / tetrahydrofuran / 1 h / -78 °C

5.2: 73 percent / tetrahydrofuran / 2 h / -78 - 20 °C

6.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure

7.1: pyridinium p-toluenesulfonate / benzene / 5 h / 65 °C

With lithium borohydride; hydrogen; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; benzene; 5.2: Heathcock's aldol reaction;
DOI:10.1021/jm0204136