(R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-oxazolidin-2-one

Base Information

Chemical Name:(R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-oxazolidin-2-one
CAS No.:725268-46-2
Molecular Formula:C₃₄H₃₉NO₅
Molecular Weight:541.687
Hs Code.:

Synonyms:(R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-oxazolidin-2-one

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Chemical Property of (R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-oxazolidin-2-one

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Technology Process of (R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-oxazolidin-2-one

There total 6 articles about (R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-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: 94.0%

: 74-88-4
methyl iodide

: 725268-45-1
(R)-4-Benzyl-3-[3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-propionyl]-oxazolidin-2-one

: 725268-46-2
(R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-oxazolidin-2-one

Guidance literature:: (R)-4-Benzyl-3-[3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-propionyl]-oxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 6h; Further stages.;
DOI:10.1016/j.tet.2004.04.072

Reference yield:

: 2-((4R,5R)-4,5-Bis-benzyloxy-cyclohex-2-enyl)-ethanol

: 725268-46-2
(R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 80 percent / p-TsNHNH₂; aq. NaOAc / 1,2-dimethoxy-ethane / 5 h / 95 °C

2.1: 92 percent / EtN₃; DMAP / CH₂Cl₂ / 4 h / 20 °C

3.1: 91 percent / dimethylsulfoxide / 4 h / 60 °C

4.1: 100 percent / KOH / ethanol; H₂O / Heating

5.1: Et₃N; pivaloyl chloride / tetrahydrofuran / 1.5 h / -78 - 0 °C

5.2: 92 percent / LiCl / tetrahydrofuran / 20 °C

6.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

6.2: 94 percent / tetrahydrofuran / 6 h / -78 °C

With dmap; potassium hydroxide; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; toluene-4-sulfonic acid hydrazide; ethyl azide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1016/j.tet.2004.04.072

Reference yield:

: 725268-59-7
3-((1R,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-propionitrile

: 725268-46-2
(R)-4-Benzyl-3-[(R)-3-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-2-methyl-propionyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / KOH / ethanol; H₂O / Heating

2.1: Et₃N; pivaloyl chloride / tetrahydrofuran / 1.5 h / -78 - 0 °C

2.2: 92 percent / LiCl / tetrahydrofuran / 20 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 94 percent / tetrahydrofuran / 6 h / -78 °C

With potassium hydroxide; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; In tetrahydrofuran; ethanol; water;
DOI:10.1016/j.tet.2004.04.072