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

Base Information

Chemical Name:(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one
CAS No.:183565-25-5
Molecular Formula:C₂₃H₃₇NO₅Si
Molecular Weight:435.636
Hs Code.:

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

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

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

There total 5 articles about (R)-4-Benzyl-3-[(2R,3S,4S)-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: 92.0%

: 104701-87-3
(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

: 101711-78-8,131685-53-5
(3R)-3-propionyl-4-benzyloxazolidin-2-one

: 183565-25-5
(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

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

Reference yield:

: 93454-85-4
(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester

: 183565-25-5
(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / DIBAL

2: 92 percent / Bu₂BOTf; DIPEA

With di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 2: Evans aldol reaction;
DOI:10.1021/ol026942l

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 183565-25-5
(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / Inert atmosphere

3.1: dimethyl sulfoxide; phosgene / dichloromethane / 2 h / -78 °C / Inert atmosphere

3.2: 1.08 h / -78 - 0 °C

4.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 0.92 h / -78 - 0 °C / Inert atmosphere

4.2: 3 h / -78 - 0 °C

With 1H-imidazole; phosgene; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: |Swern Oxidation / 4.1: |Evans Aldol Reaction;
DOI:10.1002/ejoc.202000837