4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid

Base Information

• Chemical Name: 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid
• CAS No.: 223134-87-0
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373

Synonyms:4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid

Chemical Property of 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid

Chemical Property:

• Boiling Point: 459.0±45.0 °C(Predicted)
• Density: 1.177±0.06 g/cm3(Predicted)

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

(4R,5S)-2,2-Dimethyl-4-phenyl-3,5-oxazolidinedicarboxylicAcid3-(1,1-Dimethylethyl)Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (4R,5S)-2,2-Dimethyl-4-phenyl-3,5-oxazolidinedicarboxylic Acid 3-(1,1-dimethylethyl) Ester is a reagent for preparing?1,8-naphthyridine-3-carboxamide derivatives with anticancer and anti-inflammatory activities. It can also be used to synthesize taxol derivatives for medical applications.

Technology Process of 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid

There total 7 articles about 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 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:

phenylmagnesium bromide (100-58-3) → 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid (223134-87-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Et₂AlCl / 1.) Et₂O, room temp., 15 min, 2.) Et₂O, -60 deg C, 6 h

2: 1.) H₂ / 1.) Pd(OH)2/C / 1.) MeOH, 70 psi, 3 d, 2.) 1,4-dioxane, room temp., 16 h

3: 96 percent / p-toluensulfonic acid monohydrate / methanol / 4 h / Heating

4: 91 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

5: 80 percent / (1R)-(-)-10-camphorsulfonic acid / acetone / 0.5 h / Ambient temperature

6: 86 percent / Bu₄NF / tetrahydrofuran / 1 h / Heating

7: NaIO₄, RuO₂ monohydrate, NaHCO₃ / H₂O; CCl₄; acetonitrile / Ambient temperature

With 1H-imidazole; dmap; ruthenium(IV) oxide; sodium periodate; (R)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylaluminium chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; tetrachloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0040-4020(98)00741-8

Reference yield:

N-Benzyl-N-[(R)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-hydroxylamine (192764-06-0) → 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid (223134-87-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) H₂ / 1.) Pd(OH)2/C / 1.) MeOH, 70 psi, 3 d, 2.) 1,4-dioxane, room temp., 16 h

2: 96 percent / p-toluensulfonic acid monohydrate / methanol / 4 h / Heating

3: 91 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

4: 80 percent / (1R)-(-)-10-camphorsulfonic acid / acetone / 0.5 h / Ambient temperature

5: 86 percent / Bu₄NF / tetrahydrofuran / 1 h / Heating

6: NaIO₄, RuO₂ monohydrate, NaHCO₃ / H₂O; CCl₄; acetonitrile / Ambient temperature

With 1H-imidazole; dmap; ruthenium(IV) oxide; sodium periodate; (R)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; tetrachloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0040-4020(98)00741-8

Reference yield:

(4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester (215171-13-4) → 4R,5S-1-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid (223134-87-0)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; sodium hydrogencarbonate; In tetrachloromethane; water; acetonitrile; Ambient temperature;

DOI:10.1016/S0040-4020(98)00741-8

upstream raw materials:

(4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

phenylmagnesium bromide

(2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol

(2S,3R)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-3-phenyl-1,2-propanediol

Downstream raw materials:

(4R,5S)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester

2,2-dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(5,8-dimethoxy-2,9a,10,10-tetramethyl-1,4,4a,9,9a,10-hexahydro-anthracen-1-yl) ester

2,2-dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(5,8-dimethoxy-2,10,10-trimethyl-1,4,4a,9,9a,10-hexahydro-anthracen-1-yl) ester

(4R,5S)-5-(2-Carboxy-phenylcarbamoyl)-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

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