(4S,5S)-4-((1S,2R)-2-Carboxy-1-hydroxy-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (4S,5S)-4-((1S,2R)-2-Carboxy-1-hydroxy-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
• CAS No.: 148843-21-4
• Molecular Formula: C₁₈H₂₃NO₆
• Molecular Weight: 349.384

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 13 articles about (4S,5S)-4-((1S,2R)-2-Carboxy-1-hydroxy-propyl)-5-isopropyl-2-phenyl-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: 56.0%

(4S,5S)-4-((1S,2R)-1-Hydroxy-2-methyl-3-oxo-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester → (4S,5S)-4-((1S,2R)-2-Carboxy-1-hydroxy-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (148843-21-4)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; for 0.75h; Ambient temperature;

DOI:10.1021/ja9541544

Reference yield:

(para-bromophenyl)-4-methyl-2-(E)-pentenoate (227946-96-5) → (4S,5S)-4-((1S,2R)-2-Carboxy-1-hydroxy-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (148843-21-4)

Guidance literature:

Multi-step reaction with 9 steps

1: K₂[OsO₂(OH)4]; 1,4-bis(dihydroquininyl)anthraquinone / propan-1-ol; H₂O / 20 °C

2: Ti(OiPr)4 / 20 °C

3: H₂ / Pd/C / methanol

4: 85 percent / TsOH / 1,2-dimethoxy-ethane / 4 h

5: 85 percent / LHMDS / tetrahydrofuran / -78 °C

6: dicyclohexylcarbodiimide; DMSO; CF₃COOH / pyridine

7: 60 percent / TiCl₄ / -78 - 35 °C

8: O₃; Me₂S

9: NaClO₂; NaH₂PO₄

With titanium(IV) isopropylate; sodium chlorite; sodium dihydrogenphosphate; 1,4-bis(dihydroquinidinyl)anthraquinone; dimethylsulfide; K2; hydrogen; titanium tetrachloride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; propan-1-ol; 1,2-dimethoxyethane; water; 1: Addition / 2: Esterification / 3: Hydrogenolysis / 4: Cyclization / 5: Condensation / 6: Oxidation / 7: Addition / 8: Oxidation / 9: Oxidation;

DOI:10.1002/(SICI)1521-3773(19990419)38:8<1093::AID-ANIE1093>3.0.CO;2-U

Reference yield:

(2R,3S)-2-Benzyloxycarbonylamino-3-hydroxy-4-methyl-pentanoic acid methyl ester (141970-53-8) → (4S,5S)-4-((1S,2R)-2-Carboxy-1-hydroxy-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (148843-21-4)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/C / methanol

2: 85 percent / TsOH / 1,2-dimethoxy-ethane / 4 h

3: 85 percent / LHMDS / tetrahydrofuran / -78 °C

4: dicyclohexylcarbodiimide; DMSO; CF₃COOH / pyridine

5: 60 percent / TiCl₄ / -78 - 35 °C

6: O₃; Me₂S

7: NaClO₂; NaH₂PO₄

With sodium chlorite; sodium dihydrogenphosphate; dimethylsulfide; hydrogen; titanium tetrachloride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; 1: Hydrogenolysis / 2: Cyclization / 3: Condensation / 4: Oxidation / 5: Addition / 6: Oxidation / 7: Oxidation;

DOI:10.1002/(SICI)1521-3773(19990419)38:8<1093::AID-ANIE1093>3.0.CO;2-U

upstream raw materials:

(2R)-2-Amino-3-hydroxy-4-methylpentansaeure-methylester

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

(4R,5S)-4-Formyl-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

(4S,5S)-4-Hydroxymethyl-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Downstream raw materials:

Lactacystin

omuralide

(3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid

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