(S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

Base Information

Chemical Name:(S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one
CAS No.:289619-05-2
Molecular Formula:C₂₃H₂₅NO₅
Molecular Weight:395.455
Hs Code.:

Synonyms:(S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

There total 1 articles about (S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-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: 73.0%

: 556-56-9
allyl iodid

: 139462-27-4,118949-49-8
(4S)-3-[1-oxo-2-(4-methoxybenzyloxy)ethyl]-4-benzyl-2-oxazolidinone

: 289619-05-2
(S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

Guidance literature:: (4S)-3-[1-oxo-2-(4-methoxybenzyloxy)ethyl]-4-benzyl-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

allyl iodid; In tetrahydrofuran; toluene; at -78 - -40 ℃; Further stages.;
DOI:10.1021/ol006091m

Reference yield: 94.0%

: 289619-05-2
(S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

: 760181-72-4
(R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol

Guidance literature:: With methanol; lithium borohydride; In diethyl ether; at 0 ℃; for 1.5h;
DOI:10.1016/j.tet.2004.05.045

Reference yield:

: 289619-05-2
(S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

: [(Z)-(2R,3R,8R)-8-((S)-1,3-Bis-benzyloxy-propyl)-2-ethyl-3,4,7,8-tetrahydro-2H-oxocin-3-yloxy]-triisopropyl-silane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 94 percent / LiBH₄; MeOH / diethyl ether / 1.5 h / 0 °C

2.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 1.3 g / ZnBr₂ / diethyl ether / 2 h / 0 °C

4.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

4.2: 77 percent / DMAP / tetrahydrofuran; toluene / 3 h / 20 °C

5.1: 91 percent / NaHCO₃; DDQ / CH₂Cl₂ / 5 h / 0 °C

6.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 4.5 h / 20 °C

7.1: DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

7.2: DMAP / CH₂Cl₂; hexane / -78 - 20 °C

8.1: 64 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / 20 °C

9.1: 99 percent / first generation Grubbs' catalyst / CH₂Cl₂ / 4 h / 35 °C

With 2,6-dimethylpyridine; methanol; lithium borohydride; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2.1: Swern oxidation / 3.1: Grignard reaction;
DOI:10.1016/j.tet.2004.05.045