(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

Base Information

Chemical Name:(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate
CAS No.:1383736-53-5
Molecular Formula:C₁₇H₂₁NO₃
Molecular Weight:287.359
Hs Code.:

Synonyms:(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

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Chemical Property of (4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

Chemical Property:

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Technology Process of (4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

There total 1 articles about (4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate 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:

: 7766-48-5
1-iodo-4-pentene

: 60538-17-2,62107-40-8,74272-77-8,79952-14-0,79952-15-1,82659-84-5,88336-08-7
(4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

: 1383736-53-5
(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

Guidance literature:: (4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine; In tetrahydrofuran; at -85 - -78 ℃; for 0.583333h; Inert atmosphere;

1-iodo-4-pentene; In tetrahydrofuran; at -78 - 20 ℃; for 24.5h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol301461e

Reference yield: 82.0%

: 1383736-53-5
(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

: 75-16-1
methylmagnesium bromide

: 1383736-54-6
1-((4R,5R)-5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazol-4-yl)ethanone

Guidance literature:: (4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate; With N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; for 0.0833333h; Inert atmosphere;

methylmagnesium bromide; In tetrahydrofuran; at -5 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol301461e

Reference yield:

: 1383736-53-5
(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

: C₁₆H₁₈N₄O₂

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,O-dimethylhydroxylamine*hydrochloride / tetrahydrofuran / 0.08 h / Inert atmosphere

1.2: -5 - 20 °C / Inert atmosphere

2.1: ozone / ethyl acetate / -78 °C

2.2: 8 h / Inert atmosphere; Reflux

3.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

4.1: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere

4.2: 60 °C

5.1: sodium tetrahydroborate / methanol

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); bromine; N,O-dimethylhydroxylamine*hydrochloride; silica gel; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; 3.1: Aldol condensation;
DOI:10.1021/ol301461e