3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide

Base Information

Chemical Name:3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide
CAS No.:220805-49-2
Molecular Formula:C₂₄H₃₆N₂O₅
Molecular Weight:432.56
Hs Code.:

Synonyms:3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide

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Chemical Property of 3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide

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Technology Process of 3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide

There total 11 articles about 3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide 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:

: 148906-20-1
(4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

: 220805-44-7
2R-formylpentanoic acid diethylamide

: 220805-49-2
3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide

Guidance literature:: (4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -76.5 ℃; for 0.5h;

With dimethylaluminum chloride; In tetrahydrofuran; hexane; at -76.5 ℃; for 0.666667h;

2R-formylpentanoic acid diethylamide; In tetrahydrofuran; hexane; at -81.5 - -20 ℃; for 1.08333h;
DOI:10.1021/ja991175f

Reference yield:

: 20515-15-5
methyl (2E)-4-methylpent-2-enoate

: 220805-49-2
3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 60 percent / K₂OsO₂(OH)4; hydroquinine 1,4-phthalazinediyl diether; aq. N-methylmorpholine N-oxide / 2-methyl-propan-2-ol / 49 h / 20 °C

2.1: BF₃*OEt₂ / CH₂Cl₂ / 1.83 h / 20 °C

3.1: acetyl bromide / CH₂Cl₂ / 2.5 h / 20 °C

4.1: 85 percent / sodium azide / dimethylsulfoxide / 11 h / 20 °C

5.1: H₂; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C

5.2: 89 percent / p-TsOH*H₂O / toluene / 2.75 h / Heating

6.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.5 h / -76.5 °C

6.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 0.67 h / -76.5 °C

6.3: tetrahydrofuran; hexane / 1.08 h / -81.5 - -20 °C

With hydrogenchloride; palladium dihydroxide; sodium azide; Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); Acetyl bromide; boron trifluoride diethyl etherate; hydrogen; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol; 1.1: dihydroxylation / 2.1: Condensation / 3.1: Ring cleavage / 4.1: azidation / 5.1: Hydrogenation / 5.2: Cyclization / 6.1: Metallation / 6.2: Substitution / 6.3: Condensation;
DOI:10.1021/ja991175f

Reference yield:

: 638-29-9
n-valeryl chloride

: 220805-49-2
3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.17 h / 4 °C

2.2: diisopropylethylamine / CH₂Cl₂ / 1 h / 4 °C

2.3: 85 percent / CH₂Cl₂ / 6 h / 0 - 4 °C

3.1: 90 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 48 h / 4 °C

4.1: 98 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium*BF₄; diisopropylethylamine / acetonitrile / 2 h / 0 - 4 °C

5.1: H₂; 10 percent Pd(OH)2/C / methanol / 48 h / 20 °C / 760 Torr

6.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.5 h / -76.5 °C

7.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 0.67 h / -76.5 °C

7.3: tetrahydrofuran; hexane / 1.08 h / -81.5 - -20 °C

With palladium dihydroxide; lithium hydroxide; n-butyllithium; hydrogen; dihydrogen peroxide; titanium tetrachloride; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; 1.1: Metallation / 1.2: Acylation / 2.1: complexation / 2.2: enolization / 2.3: benzyloxymethylation / 3.1: Hydrolysis / 4.1: Condensation / 5.1: Hydrogenation / 6.1: Oxidation / 7.1: Metallation / 7.2: Substitution / 7.3: Condensation;
DOI:10.1021/ja991175f