(4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Base Information

Chemical Name:(4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
CAS No.:860453-75-4
Molecular Formula:C₁₇H₂₃NO₅
Molecular Weight:321.373
Hs Code.:

Synonyms:(4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

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Chemical Property of (4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

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Technology Process of (4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

There total 1 articles about (4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 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: 81.0%

: 78-84-2
isobutyraldehyde

: 704910-29-2
methyl (4S,5R)-4,5-dihydro-2-(4-methoxyphenyl)-5-methyloxazole-4-carboxylate

: 860453-75-4
(4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Guidance literature:: methyl (4S,5R)-4,5-dihydro-2-(4-methoxyphenyl)-5-methyloxazole-4-carboxylate; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

With zinc(II) chloride; In tetrahydrofuran; toluene; at -78 ℃; for 0.166667h;

isobutyraldehyde; In tetrahydrofuran; toluene; at -78 ℃; for 8h;
DOI:10.1021/ja052376o

Reference yield: 95.0%

: 860453-75-4
(4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

: 69739-34-0
t-butyldimethylsiyl triflate

: 860453-67-4
(4S,5R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 6h;
DOI:10.1021/ja052376o

Reference yield:

: 860453-75-4
(4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

: 860453-73-2
(2R,3S,4R)-4-(2-Chloro-ethyl)-3-hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid benzylamide

Guidance literature:: Multi-step reaction with 14 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

2.1: NaCNBH₃; Et₃N; AcOH / 24 h / 40 °C

3.1: 5.0 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -78 °C

4.1: 79 percent / triisobutylamine / acetonitrile / 72 h / 23 °C

5.1: Ti(OiPr)4; c-C₅H₉MgCl / diethyl ether; various solvent(s) / 0.5 h / -40 °C

5.2: I₂ / tetrahydrofuran; diethyl ether; various solvent(s) / 4 h / -40 - 23 °C

5.3: 85 percent / Et₃N / CH₂Cl₂ / 0.5 h

6.1: imidazole / dimethylformamide / 1 h / 0 °C

7.1: 3.0 g / NaI / acetone / 6 h / 60 °C

8.1: 93 percent / Et₂AlCl; Bu₃SnH; Et₃B / air / toluene; hexane / 3 h / -78 °C

9.1: 90 percent / KHCO₃; KF; aq. H₂O₂ / methanol; tetrahydrofuran / 18 h / 23 °C

10.1: 84 percent / CAN; H₂O / acetonitrile / 0.5 h / 0 °C

11.1: MeTeAlMe₂ / toluene / 12 h / 23 °C

12.1: 315 mg / PPh₃Cl₂; pyridine / acetonitrile / 12 h / 23 °C

13.1: 82 percent / aq. HF / acetonitrile / 72 h / 23 °C

14.1: 98 percent / tetrahydrofuran / 12 h / 23 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; potassium fluoride; oxalyl dichloride; ammonium cerium(IV) nitrate; triisobutylamine; triethyl borane; Me₂AlTeMe; hydrogen fluoride; water; dihydrogen peroxide; tri-n-butyl-tin hydride; diethylaluminium chloride; cyclopentylmagnesium chloride; sodium cyanoborohydride; potassium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; sodium iodide; dichlorotriphenylphosphorane; air; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Swern oxidation;
DOI:10.1021/ja052376o