(R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-oxazolidin-2-one

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Chemical Name:(R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-oxazolidin-2-one
CAS No.:284471-61-0
Molecular Formula:C₃₄H₄₇NO₆Si
Molecular Weight:593.836
Hs Code.:

Synonyms:(R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-oxazolidin-2-one

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Chemical Property of (R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-oxazolidin-2-one

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Technology Process of (R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-oxazolidin-2-one

There total 5 articles about (R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-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: 89.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 284471-58-5
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

: 284471-61-0
(R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-oxazolidin-2-one

Guidance literature:: With 2,6-dimethylpyridine;
DOI:10.1021/ja0007197

Reference yield:

: 58931-16-1,88981-35-5,110339-28-1
(R)-1-benzyloxypent-4-en-2-ol

: 284471-61-0
(R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / NaH / tetrahydrofuran / 14 h / 25 °C

2.1: Et₃N / diethyl ether / 1 h / 0 °C

3.1: nBuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 15.3 g / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C

4.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 2.5 h / -78 °C

4.2: 65 percent / CH₂Cl₂ / 1 h / -78 °C

5.1: 89 percent / 2,6-lutidine

With 2,6-dimethylpyridine; n-butyllithium; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Alkylation / 2.1: Acylation / 3.1: Metallation / 3.2: Acylation / 4.1: complexation / 4.2: aldol reaction / 5.1: silylation;
DOI:10.1021/ja0007197

Reference yield:

: 239075-68-4
(R)-1-(benzyloxymethyl)but-3-enyl-1-oxyacetic acid

: 284471-61-0
(R)-4-Benzyl-3-[(2R,3S)-2-((R)-1-benzyloxymethyl-but-3-enyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-enoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N / diethyl ether / 1 h / 0 °C

2.1: nBuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 15.3 g / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C

3.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 2.5 h / -78 °C

3.2: 65 percent / CH₂Cl₂ / 1 h / -78 °C

4.1: 89 percent / 2,6-lutidine

With 2,6-dimethylpyridine; n-butyllithium; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Acylation / 2.1: Metallation / 2.2: Acylation / 3.1: complexation / 3.2: aldol reaction / 4.1: silylation;
DOI:10.1021/ja0007197