158722-22-6

Usage

Uses

Used in Organic Synthesis:
(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid is utilized as a building block in organic synthesis for the creation of other complex organic compounds. Its unique structure allows for the formation of various chemical entities, contributing to the advancement of organic chemistry.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid serves as a potential lead compound for the development of new pharmaceutical agents. Its specific molecular configuration and properties may offer novel therapeutic avenues, warranting further research into its medicinal applications and potential efficacy in treating various health conditions.
Further exploration of the chemical properties and potential applications of (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid is essential to uncover its full potential across scientific and industrial domains.

InChI:InChI=1S/C16H13NO3/c18-16(19)14-13(11-7-3-1-4-8-11)17-15(20-14)12-9-5-2-6-10-12/h1-10,13-14H,(H,18,19)/t13-,14+/m0/s1

Synthetic route

(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester (146848-91-1) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
With sodium hydroxide	96%
With sodium hydroxide In methanol; water at 20℃;	86%
With sodium hydroxide In methanol; water at 20℃; for 5h;	86%
With hydrogenchloride; sodium hydroxide	76%
With sodium hydroxide In water

(-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (1251618-11-7) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Stage #1: (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate With water; potassium carbonate In methanol at 20℃; Stage #2: With hydrogenchloride In water pH=2;	81%

(-)-menthyl (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (1251618-08-2) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Stage #1: (-)-menthyl (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate With water; potassium carbonate In methanol at 20℃; for 5h; Stage #2: With hydrogenchloride In water pH=2;	79%

(4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline (216769-41-4) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
With ruthenium trichloride; sodium periodate; sodium hydrogencarbonate In tetrachloromethane; water; acetonitrile for 48h;	78%
With ruthenium trichloride; sodium periodate; sodium hydrogencarbonate In tetrachloromethane; water; acetonitrile for 48h; Oxidation; degradation;

sodium periodate (NaIO4) + (4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline (216769-41-4) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
With sodium hydrogencarbonate; ruthenium(III)chloride In tetrachloromethane; water; acetonitrile	75%

N-((1S,2S,3R)-3,4-Dihydroxy-2-iodo-1-phenyl-butyl)-benzamide (229648-90-2) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
With sodium chlorite; sodium periodate; sodium dihydrogenphosphate 1.) acetone, H2O, RT, 2.) 2-methyl-2-butene, t-BuOH, H2O, RT; Yield given; Multistep reaction;

(2R,3S)-2,3-dihydroxy-3-phenyl-propionic acid (56816-81-0) + benzonitrile (100-47-0) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
With sulfuric acid at -10 - 20℃;

(4S,5R)-[2,4-diphenyl-(5-hydroxymethyl)]-1,3-oxazoline (688362-45-0) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
With pyridinium chlorochromate In N,N-dimethyl-formamide for 2h;

(2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / H2O View Scheme
Multi-step reaction with 2 steps 1: 41 percent / toluene / 8 h / Heating 2: 86 percent / NaOH / methanol; H2O / 20 °C View Scheme

orthobenzoic acid trimethyl ester (707-07-3) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / H2O View Scheme
Multi-step reaction with 2 steps 1: 41 percent / toluene / 8 h / Heating 2: 86 percent / NaOH / methanol; H2O / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 41 percent / toluene / 8 h / Heating 2: 86 percent / NaOH / methanol; H2O / 20 °C View Scheme

(1S)-N-1-(1-phenyl-2,3-dihydroxypropyl)benzamide → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: imidazole / dimethylformamide / 14 h 2: 99 percent / Deoxo-Fluor(R) / CH2Cl2 / 0.5 h / -20 °C 3: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h 4: pyridinium chlorochromate / dimethylformamide / 2 h View Scheme

(4S,5R)-5-({[1-(tert-butyl)-1,1-diphenylsilyl]-oxy}-methyl)-2,4-diphenyl-1,3-oxazoline (688362-44-9) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h 2: pyridinium chlorochromate / dimethylformamide / 2 h View Scheme

(S)-N-1-(3-[(1-tert-butyl)-1,1-diphenylsilyl]oxy-2-oxo-1-phenylpropyl)benzamide (688362-43-8) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / L-Selectride / tetrahydrofuran / 4 h / 0 °C 2: 99 percent / Deoxo-Fluor(R) / CH2Cl2 / 0.5 h / -20 °C 3: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h 4: pyridinium chlorochromate / dimethylformamide / 2 h View Scheme

(1S)-N-1-(3-{[(1-tert-butyl)-1,1-diphenylsilyl]oxy}-2-hydroxy-1-phenylpropyl)benzamide → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 84 percent / CrO3; H2SO4; H2O / acetone / 0.5 h 2: 99 percent / L-Selectride / tetrahydrofuran / 4 h / 0 °C 3: 99 percent / Deoxo-Fluor(R) / CH2Cl2 / 0.5 h / -20 °C 4: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h 5: pyridinium chlorochromate / dimethylformamide / 2 h View Scheme

(1S,2S)-N-1-(3-{[(1-tert-butyl)-1,1-diphenylsilyl]oxy}-2-hydroxy-1-phenylpropyl)benzamide (688362-79-0) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / Deoxo-Fluor(R) / CH2Cl2 / 0.5 h / -20 °C 2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h 3: pyridinium chlorochromate / dimethylformamide / 2 h View Scheme

(2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid (136561-53-0) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 41 percent / toluene / 8 h / Heating 2: 86 percent / NaOH / methanol; H2O / 20 °C View Scheme
Multi-step reaction with 2 steps 1: orthobenzoic acid trimethyl ester / toluene / 8 h / 110 °C 2: sodium hydroxide / methanol; water / 5 h / 20 °C View Scheme

benzoyl chloride (98-88-4) + 1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol bound on Rink resin → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaHCO3 / methanol / 0 °C 2: 1.) NaIO4, 2.) NaClO2, NaH2PO4 / 1.) acetone, H2O, RT, 2.) 2-methyl-2-butene, t-BuOH, H2O, RT View Scheme

(2S,3E)-4-phenylbut-3-ene-1,2-diol (229648-88-8) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) DBU, 2.) IBr, K2CO3 / 1.) CH3CN, -30 deg C, 2.) CH3CN, -30 to -10 deg C 2: 6N HCl / methanol / Ambient temperature 3: NaHCO3 / methanol / 0 °C 4: 1.) NaIO4, 2.) NaClO2, NaH2PO4 / 1.) acetone, H2O, RT, 2.) 2-methyl-2-butene, t-BuOH, H2O, RT View Scheme

(2R,3S,4S)-4-Amino-3-iodo-4-phenyl-butane-1,2-diol → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaHCO3 / methanol / 0 °C 2: 1.) NaIO4, 2.) NaClO2, NaH2PO4 / 1.) acetone, H2O, RT, 2.) 2-methyl-2-butene, t-BuOH, H2O, RT View Scheme

2,2,2-Trichloro-acetimidic acid (4S,5S,6R)-5-iodo-4-phenyl-2-trichloromethyl-5,6-dihydro-4H-[1,3]oxazin-6-ylmethyl ester (229648-89-9) → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 6N HCl / methanol / Ambient temperature 2: NaHCO3 / methanol / 0 °C 3: 1.) NaIO4, 2.) NaClO2, NaH2PO4 / 1.) acetone, H2O, RT, 2.) 2-methyl-2-butene, t-BuOH, H2O, RT View Scheme

(1S,2R,5S)-(+)-menthyl (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
With hydrogenchloride; potassium carbonate In methanol; water

(2R,3R)-3-phenyloxirane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 4 h / -78 °C / Inert atmosphere 2.1: water; potassium carbonate / methanol / 5 h / 20 °C 2.2: pH 2 View Scheme

(2S,3S)-3-phenyloxirane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester → (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 4 h / -78 °C / Inert atmosphere 2.1: water; potassium carbonate / methanol / 20 °C 2.2: pH 2 View Scheme

diazomethane (186581-53-3, 908094-01-9) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester (146848-91-1)

Conditions	Yield
In diethyl ether	100%
In diethyl ether for 0.166667h; Methylation; esterification;
In diethyl ether; N,N-dimethyl-formamide

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) + 4-(4,6-diphenoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → N-methylmorpholine hydrochloride (3651-67-0)

Conditions	Yield
In tetrahydrofuran for 12h;	100%

4-methyl-morpholine (109-02-4) + 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → N-methylmorpholine hydrochloride (3651-67-0)

Conditions	Yield
Stage #1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 0 - 5℃; for 0.5h; Stage #2: (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid In tetrahydrofuran at 0 - 20℃; for 12h;	100%

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) + 6,7-dehydro-baccatin III (158830-50-3) → C47H47NO12 (172666-19-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene Ambient temperature;	97%

7-(triethylsilyl)baccatin III (115437-21-3) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → 7-(triethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydrooxazol-5-yl)carbonyl]baccatin (158722-23-7)

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In toluene for 0.5h; Ambient temperature;	95%
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In toluene at 0 - 20℃; for 1.16667h;	93%

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) + 15-O-t-butyldimethylsilyl-lactarorufin B (374536-28-4) → (4S,5R)-2,4-diphenyl-4,5-dihydro-oxazol-5-carboxylic acid (15-O-t-butyldimethylsilyl-lactarorufin B)-8-yl ester (374536-35-3)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	95%

7-triethylsilyl-1-deoxybaccatin III (1411663-99-4) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → 7-triethylsilyl-13-[(5R)-2,4-diphenyl-2,5-dihydrooxazole-5-carboxylic]-1-deoxybaccatin III (1411664-02-2)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In toluene at 50℃;	94%

7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III (95603-44-4) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C51H49Cl6NO16 (186596-01-0)

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In toluene at 20℃; for 2h;	92%

C38H54O10Si + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C54H65NO12Si

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In (2)H8-toluene at 20℃; for 0.0333333h;	90%

13-oxo-14β-hydroxy-7-O-triethylsilyl-9,10-O-isopropylidene-1-deoxybaccatin VI + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → 14β-O-[(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carbonyl]-13-oxo-7-O-triethylsilyl-9,10-O-isopropylidene-1-deoxybaccatin VI

Conditions	Yield
Stage #1: 13-oxo-14β-hydroxy-7-O-triethylsilyl-9,10-O-isopropylidene-1-deoxybaccatin VI; (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid With dmap In toluene at 20℃; for 0.166667h; Stage #2: With dicyclohexyl-carbodiimide In toluene	90%

C38H56O12Si + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C47H53NO12

Conditions	Yield
Stage #1: C38H56O12Si; (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid With dmap; 1,3-Dicyclohexylurea In toluene at 20℃; for 3h; Stage #2: With acetic acid In toluene for 0.75h;	86%

7,9,10,13-four(deacetyl)-9,10-O-isopropylidene-1-deoxybaccatin VI + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C48H53NO11

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃;	83%

C34H44O11 + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C50H55NO13

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene for 2h;	80%

C32H42O11 + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C48H53NO13

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene for 1.5h;	79%

15-dihydroatractyligenin methyl ester (43059-73-0) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C36H39NO6 (926026-11-1)

Conditions	Yield
Stage #1: (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.25h; Stage #2: 15-dihydroatractyligenin methyl ester In dichloromethane at 20℃; for 3h; Further stages.;	73%

repin + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C35H33NO9 (861659-91-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	72%

C38H54O10Si + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C48H53NO13

Conditions	Yield
Stage #1: C38H54O10Si; (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 0.0333333h; Stage #2: With hydrogenchloride In methanol; water at 20 - 60℃; for 4h; pH=3 - 4;	42%

C40H60O11Si + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → C50H59NO14

Conditions	Yield
Stage #1: C40H60O11Si; (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 0.0333333h; Stage #2: With hydrogenchloride In methanol; water at 20 - 60℃; for 4h; pH=3 - 4;	33%

diazomethane (186581-53-3, 908094-01-9) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → (4R,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid methyl ester (209736-09-4)

Conditions	Yield
In methanol at 0℃; Yield given;

furanol (94061-58-2) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR)-6,6,8-trimethyl-4,4a,5,6,7,9-hexahydro-2-oxa-cyclopenta[f]azulen-4-yl ester (395664-53-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

furandiol (59684-34-3) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR,7aS,8S)-8-hydroxy-6,6,8-trimethyl-4,4a,5,6,7,7a,8,9-octahydro-2-oxa-cyclopenta[f]azulen-4-yl ester (395664-55-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

3-O-ethylfurandiol (71305-68-5) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR,7aS,8S)-8-ethoxy-6,6,8-trimethyl-4,4a,5,6,7,7a,8,9-octahydro-2-oxa-cyclopenta[f]azulen-4-yl ester (395664-64-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

4,4α,5,6,7,7α,8,9-octahydro-4,8-dihydroxy-6,6,8-trimethyl-(4S,4αR,7αS,8S)-azuleno[5,6-c]furan-1(3H)-one (35008-20-9) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR,7aS,8S)-8-hydroxy-6,6,8-trimethyl-1-oxo-1,3,4,4a,5,6,7,7a,8,9-decahydro-2-oxa-cyclopenta[f]azulen-4-yl ester (395664-72-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

anhydro deconjugated lactarorufin A (58757-92-9) + (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid (158722-22-6) → (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR)-6,6,8-trimethyl-1-oxo-1,3,4,4a,5,6,7,9-octahydro-2-oxa-cyclopenta[f]azulen-4-yl ester (395664-70-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

Upstream product

• 1251618-08-2 (-)-menthyl (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate 
• 1251618-11-7 (-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate 
• 216769-41-4 (4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline 
• 229648-89-9 2,2,2-Trichloro-acetimidic acid (4S,5S,6R)-5-iodo-4-phenyl-2-trichloromethyl-5,6-dihydro-4H-[1,3]oxazin-6-ylmethyl ester 
• 229648-88-8 (2S,3E)-4-phenylbut-3-ene-1,2-diol 
• 98-88-4 benzoyl chloride 
• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 688362-79-0 (1S,2S)-N-1-(3-{[(1-tert-butyl)-1,1-diphenylsilyl]oxy}-2-hydroxy-1-phenylpropyl)benzamide 
• 688362-43-8 (S)-N-1-(3-[(1-tert-butyl)-1,1-diphenylsilyl]oxy-2-oxo-1-phenylpropyl)benzamide 
• 688362-44-9 (4S,5R)-5-({[1-(tert-butyl)-1,1-diphenylsilyl]-oxy}-methyl)-2,4-diphenyl-1,3-oxazoline 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 688362-45-0 (4S,5R)-[2,4-diphenyl-(5-hydroxymethyl)]-1,3-oxazoline 
• 56816-81-0 (2R,3S)-2,3-dihydroxy-3-phenyl-propionic acid 

Downstream Products

• 172666-19-2 C₄₇H₄₇NO₁₂ 
• 146848-91-1 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester 
• 395664-72-9 (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR,7aS,8S)-8-hydroxy-6,6,8-trimethyl-1-oxo-1,3,4,4a,5,6,7,7a,8,9-decahydro-2-oxa-cyclopenta[f]azulen-4-yl ester 
• 395664-78-5 (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR,7aS,8S)-8-hydroxy-6,6,8-trimethyl-3-oxo-1,3,4,4a,5,6,7,7a,8,9-decahydro-2-oxa-cyclopenta[f]azulen-4-yl ester 
• 395664-47-8 (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (1aS,3aS,6aS,6bR)-1a-formyl-5,5,6b-trimethyl-1,1a,3a,4,5,6,6a,6b-octahydro-cyclopropa[e]inden-2-ylmethyl ester 
• 395664-51-4 C₃₁H₃₃NO₆ 
• 395664-49-0 C₃₁H₃₃NO₆ 
• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 3651-67-0 N-methylmorpholine hydrochloride 
• 709038-57-3 (2'S,3'S)-3'-N-benzoylamino-2'-deoxy-2'-thioacetyl-7,10-di-(2,2,2-trichloroethyloxycarbonyl)paclitaxel 
• 709038-58-4 (2'S,3'S)-10-deacetyl-2'-deoxy-2'-epi-acetylmercaptopaclitaxel 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 

Relevant academic research and scientific papers

Paclitaxel compounds with modified C-13 and C-14 position structure and preparing method of paclitaxel compounds

The invention relates to a paclitaxel analogue with modified C-13 and C-14 positions and a preparing method of the paclitaxel analogue. The structural formula of the analogue is shown in the description. Different side chains are introduced into the C-13 position and the C-14 position of taxanes of 1-dehydroxybaccatin VI, the annular framework and necessary functional groups of paclitaxel are reserved, paclitaxel compounds are enriched, the obtained compounds have the natural anti-cancer biological activity of natural paclitaxel, certain application prospects on the aspect of reducing the toxic and side effects of natural paclitaxel are achieved, and meanwhile it is highly beneficial for studying the activity structure-function relationship of the compounds. The compounds a, b, c, d and taxol have a suppressing effect on the in-vitro proliferation of the A 549 lung cancer cells, A 2780 ovarian carcinoma cells and HL-60 promyelocytic leukemia cells of the human body.

Substituent effect on the asymmetric induction with (1R,2S,5R)-and (1S,2R,5S)-menthol auxiliaries

Substituted benzaldehydes reacts in cis-diastcrcoselective manner with mentliyl haloacetates in the presence of phase transfer catalyst and a base in THF at room temperature to give the corresponding 3-arvloxirane-2-carboxvlates (2/3a-h) in moderate to high yields The magnitude of asymmetric induction in the latter reaction was quantified by a Hammett type equation log(2/3)x = ρσr - log(2/3)X-H The stereochemistry of compounds 2 and 3 was elucidated b correlation with (4S. 5R)-2.4-diphenyll-4,5- dihydrooxazole-5-carboxylic acid (+)-8 as well as its enantiomer (-)-8.

Enantioselective synthesis of 1-aryl-2-propenylamines: A new approach to a stereoselective synthesis of the Taxol side chain

A variety of substituted 1-aryl-2-propenylamines of high enantiomeric purity were prepared via lipase-catalysed resolution of the corresponding racemates. (R)-1-Phenyl-2-propenylamine was further synthesised into (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoic acid methyl ester, the side chain of Taxol.

Synthesis and Antifeedant Properties of N-Acylphenylisoserinates of Lactarius Sesquiterpenoid Alcohols

The esterification of various sesquiterpenoid alcohols of Lactarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol), N-acetyl-[2R,3S]-phenylisoserine and N-tert-butoxy-[2R,3S]-phenylisoserine (side chain of Taxotere) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium, Sitophylus granarius and Rhizoperta dominica were measured. The introduction of the ester moiety in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects.

Improved large-scale synthesis of phenylisoserine and the taxol C-13 side chain

Dihydrodihydroxycinnamic acids and their esters react with acetonitrile or benzonitrile in the presence of sulfuric acid to afford the corresponding syn-β-amino-α-hydroxypropionic acid derivatives. High yields and diastereoselectivity of this transformation allows preparation of various phenylisoserine derivatives on a practical scale.

Synthesis and antifeedant properties of N-benzoylphenylisoserinates of Lactarius sesquiterpenoid alcohols

The esterification of various sesquiterpenoid alcohols of Lactarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium and Sitophylus granarius were measured. The introduction of the taxol side chain in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects.

Synthesis of N-benzoylphenylisoserinates of lactarorufin B (a sesquiterpene of Lactarius origin) and its derivatives

Lactarorufin B, which is a Lactarius sesquiterpene possessing primary, secondary and tertiary hydroxyl groups on its lactarane skeleton, was selectively transformed into (2′R,3′S)-N-benzoylphenylisoserinates, using protective group methodology described below.

Intermediary compounds for the hemisynthesis of taxanes and preparation processes therefor

The present invention relates to new intermediates for the semisynthesis of taxanes and their preparation processes. It relates to derivatives of oxazolidines or oxazolidinones, as well as to new derivatives of baccatine III. The general process for the synthesis of taxanes according to the invention enables to obtain a product such as PACLITAXEL in only five steps from products available in the market, compared to nine steps in general, for processes of the prior art.

Process for the preparation of oxazoline compound

The present invention relates to a process for the preparation of an oxazoline compound which is easily chemically converted to a beta-amino-alpha-hydroxy acid or a gamma-amino-beta-hydroxy acid. The method comprises producing a compound of the following formula (4) using alpha -amino acid. The produced compound (4) is subjected to an intramolecular cyclization to produce an oxazoline compound of the following formula (3). The oxazoline compound (3) is oxidized at a vinyl group with RuCl3 or NaIO4 to produce an oxazoline compound of the following formula (1) which is easily chemically converted to a beta-amino-alpha-hydroxy acid. Alternatively, the oxazoline compound (3) may also be treated with 9-borabiclo[3.3.1]nonane such that a hydroxy group is introduced into the end of the vinyl group of the oxazoline compound(3). The introduced end hydroxy group is oxidized with RuCl3 or NaIO4 to produce an oxazoline compound of the following formula (2) which is easily chemically converted to a gamma-amino-hydroxy acid.

An enantiocontrolled synthesis of the masked taxol C-13 side chain, oxazoline carboxylic acid

Oxazoline carboxylic acid 6 as the taxol side chain precursor has been efficiently synthesized via the intramolecular iodoamidation of allylic trichloroacetimidate derived from trans-olefinic diol 1.