3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone

Base Information

Chemical Name:3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone
CAS No.:155295-76-4
Molecular Formula:C₂₉H₃₅NO₅
Molecular Weight:477.601
Hs Code.:

Synonyms:3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone

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Chemical Property of 3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone

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Technology Process of 3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone

There total 5 articles about 3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone 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:

: 104266-88-8
(4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one

: 155295-76-4
3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / Pd(OAc)2 / diethyl ether / 0.5 h / 0 °C

2.1: i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.2: 51 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1 h / -15 °C

3.2: CH₂Cl₂ / 1 h / -78 - -10 °C

4.1: NaBH(OAc)3 / acetic acid / 1 h / 25 °C

5.1: 81 mg / p-TsOH / dimethylformamide / 1 h / 25 °C

With n-butyllithium; titanium tetrachloride; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1.1: Cycloaddition / 2.1: Metallation / 2.2: Acetylation / 3.1: Metallation / 3.2: Condensation / 4.1: Reduction / 5.1: Cyclization;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 77-76-9
2,2-dimethoxy-propane

: (S)-4-Benzyl-3-((2R,3R,5S)-2-cyclopropylmethyl-3,5-dihydroxy-6-phenyl-hexanoyl)-oxazolidin-2-one

: 155295-76-4
3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 25 ℃; for 1h;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 155295-65-1,289677-11-8
3-(3-cyclopropyl-1-oxopropyl)-4(S)-phenylmethyl-2-oxazolidinone

: 155295-76-4
3-[2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenyl-1-oxohexyl]-4(S)-(phenylmethyl)-2-oxazolidinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

1.2: 51 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1 h / -15 °C

2.2: CH₂Cl₂ / 1 h / -78 - -10 °C

3.1: NaBH(OAc)3 / acetic acid / 1 h / 25 °C

4.1: 81 mg / p-TsOH / dimethylformamide / 1 h / 25 °C

With n-butyllithium; titanium tetrachloride; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Acetylation / 2.1: Metallation / 2.2: Condensation / 3.1: Reduction / 4.1: Cyclization;
DOI:10.1016/S0968-0896(98)80011-4