(4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone

Base Information

• Chemical Name: (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone
• CAS No.: 413598-51-3
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358

Synonyms:(4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone

Chemical Property of (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone

Chemical Property:

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Technology Process of (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone

There total 2 articles about (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-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: 62.0%

(3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) + crotonaldehyde (123-73-9,4170-30-3) → (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone (413598-51-3)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether; at -78 ℃;

DOI:10.1021/ol010302l

Reference yield: 62.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) + (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone (413598-51-3)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1016/j.tet.2004.06.142

Reference yield: 97.0%

Benzyloxymethyl chloride (3587-60-8) + (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone (413598-51-3) → (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-phenylmethoxymethoxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone (1019107-73-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/jo800076f

upstream raw materials:

(3R)-3-propionyl-4-benzyloxazolidin-2-one

crotonaldehyde

trans-Crotonaldehyde

Downstream raw materials:

(R)-4-Benzyl-3-((E)-(2S,3S)-3-methoxymethoxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one

Toluene-4-sulfonic acid (E)-(2R,3S)-3-methoxymethoxy-2-methyl-hex-4-enyl ester

(2S,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde

(E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

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