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158722-22-6

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158722-22-6 Usage

General Description

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid is a chemical compound with a molecular formula C17H15NO3. It is an oxazole derivative with a carboxylic acid group, and it exists as a chiral molecule with the (4S,5R) configuration. (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid has potential applications in the field of organic synthesis and pharmaceuticals due to its unique molecular structure and properties. Its specific uses may include serving as a building block for the synthesis of other organic compounds or as a potential lead compound for the development of new pharmaceutical agents. Further research and exploration of the chemical properties and potential applications of (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid may reveal its full potential in various scientific and industrial fields.

Check Digit Verification of cas no

The CAS Registry Mumber 158722-22-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,8,7,2 and 2 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 158722-22:
(8*1)+(7*5)+(6*8)+(5*7)+(4*2)+(3*2)+(2*2)+(1*2)=146
146 % 10 = 6
So 158722-22-6 is a valid CAS Registry Number.
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

158722-22-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name (4S,5R)-2,4-Diphenyl-4,5-dihydrooxazole-5-carboxylic acid

1.2 Other means of identification

Product number -
Other names (4S,5R)-2,4-Diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:158722-22-6 SDS

158722-22-6Synthetic route

(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester
146848-91-1

(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide96%
With sodium hydroxide In methanol; water at 20℃;86%
With sodium hydroxide In methanol; water at 20℃; for 5h;86%
With hydrogenchloride; sodium hydroxide76%
With sodium hydroxide In water
(-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate
1251618-11-7

(-)-menthyl (4S,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(-)-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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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)

sodium periodate (NaIO4)

(4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline
216769-41-4

(4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate; ruthenium(III)chloride In tetrachloromethane; water; acetonitrile75%
N-((1S,2S,3R)-3,4-Dihydroxy-2-iodo-1-phenyl-butyl)-benzamide
229648-90-2

N-((1S,2S,3R)-3,4-Dihydroxy-2-iodo-1-phenyl-butyl)-benzamide

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(2R,3S)-2,3-dihydroxy-3-phenyl-propionic acid

benzonitrile
100-47-0

benzonitrile

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid at -10 - 20℃;
(4S,5R)-[2,4-diphenyl-(5-hydroxymethyl)]-1,3-oxazoline
688362-45-0

(4S,5R)-[2,4-diphenyl-(5-hydroxymethyl)]-1,3-oxazoline

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
With pyridinium chlorochromate In N,N-dimethyl-formamide for 2h;
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

(2R,3S)-3-phenylisoserine hydrochloride

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

orthobenzoic acid trimethyl ester

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(1S)-N-1-(1-phenyl-2,3-dihydroxypropyl)benzamide

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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)-5-({[1-(tert-butyl)-1,1-diphenylsilyl]-oxy}-methyl)-2,4-diphenyl-1,3-oxazoline

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(S)-N-1-(3-[(1-tert-butyl)-1,1-diphenylsilyl]oxy-2-oxo-1-phenylpropyl)benzamide

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(1S,2S)-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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

benzoyl chloride

1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol bound on Rink resin

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(2S,3E)-4-phenylbut-3-ene-1,2-diol

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

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

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; potassium carbonate In methanol; water
(2R,3R)-3-phenyloxirane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

(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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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

(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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

Conditions
ConditionsYield
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
(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid
158722-22-6

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester
146848-91-1

(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester

Conditions
ConditionsYield
In diethyl ether100%
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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

4-(4,6-diphenoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

4-(4,6-diphenoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

N-methylmorpholine hydrochloride
3651-67-0

N-methylmorpholine hydrochloride

Conditions
ConditionsYield
In tetrahydrofuran for 12h;100%
4-methyl-morpholine
109-02-4

4-methyl-morpholine

2-chloro-4,6-dimethoxy-1 ,3,5-triazine
3140-73-6

2-chloro-4,6-dimethoxy-1 ,3,5-triazine

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

N-methylmorpholine hydrochloride
3651-67-0

N-methylmorpholine hydrochloride

Conditions
ConditionsYield
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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

6,7-dehydro-baccatin III
158830-50-3

6,7-dehydro-baccatin III

C47H47NO12
172666-19-2

C47H47NO12

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In toluene Ambient temperature;97%
7-(triethylsilyl)baccatin III
115437-21-3

7-(triethylsilyl)baccatin III

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

7-(triethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydrooxazol-5-yl)carbonyl]baccatin
158722-23-7

7-(triethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydrooxazol-5-yl)carbonyl]baccatin

Conditions
ConditionsYield
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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

15-O-t-butyldimethylsilyl-lactarorufin B
374536-28-4

15-O-t-butyldimethylsilyl-lactarorufin B

(4S,5R)-2,4-diphenyl-4,5-dihydro-oxazol-5-carboxylic acid (15-O-t-butyldimethylsilyl-lactarorufin B)-8-yl ester
374536-35-3

(4S,5R)-2,4-diphenyl-4,5-dihydro-oxazol-5-carboxylic acid (15-O-t-butyldimethylsilyl-lactarorufin B)-8-yl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;95%
7-triethylsilyl-1-deoxybaccatin III
1411663-99-4

7-triethylsilyl-1-deoxybaccatin III

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

7-triethylsilyl-13-[(5R)-2,4-diphenyl-2,5-dihydrooxazole-5-carboxylic]-1-deoxybaccatin III
1411664-02-2

7-triethylsilyl-13-[(5R)-2,4-diphenyl-2,5-dihydrooxazole-5-carboxylic]-1-deoxybaccatin III

Conditions
ConditionsYield
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

7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C51H49Cl6NO16
186596-01-0

C51H49Cl6NO16

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In toluene at 20℃; for 2h;92%
C38H54O10Si

C38H54O10Si

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C54H65NO12Si

C54H65NO12Si

Conditions
ConditionsYield
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

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

14β-O-[(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carbonyl]-13-oxo-7-O-triethylsilyl-9,10-O-isopropylidene-1-deoxybaccatin VI

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
ConditionsYield
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

C38H56O12Si

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C47H53NO12

C47H53NO12

Conditions
ConditionsYield
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

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C48H53NO11

C48H53NO11

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃;83%
C34H44O11

C34H44O11

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C50H55NO13

C50H55NO13

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In toluene for 2h;80%
C32H42O11

C32H42O11

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C48H53NO13

C48H53NO13

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In toluene for 1.5h;79%
15-dihydroatractyligenin methyl ester
43059-73-0

15-dihydroatractyligenin methyl ester

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C36H39NO6
926026-11-1

C36H39NO6

Conditions
ConditionsYield
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

repin

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C35H33NO9
861659-91-8

C35H33NO9

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;72%
C38H54O10Si

C38H54O10Si

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C48H53NO13

C48H53NO13

Conditions
ConditionsYield
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

C40H60O11Si

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

C50H59NO14

C50H59NO14

Conditions
ConditionsYield
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%
(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid
158722-22-6

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

(4R,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid methyl ester
209736-09-4

(4R,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid methyl ester

Conditions
ConditionsYield
In methanol at 0℃; Yield given;
furanol
94061-58-2

furanol

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

(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

(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

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
furandiol
59684-34-3

furandiol

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

(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

(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

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
3-O-ethylfurandiol
71305-68-5

3-O-ethylfurandiol

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

(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

(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

Conditions
ConditionsYield
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

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

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

(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

(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

Conditions
ConditionsYield
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

anhydro deconjugated lactarorufin A

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

(4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid

(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

(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

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

158722-22-6Relevant articles and documents

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

-

Page/Page column 17, (2017/10/09)

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.

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

Kopczacki,Gumulka,Masnyk,Sarosiek,Barycki,Ignacak,Zochowski,Grabarczyk,Nowak,Daniewski

, p. 89 - 108 (2007/10/03)

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

Voronkov, Michael V.,Gontcharov, Alexander V.,Wang, Zhi-Min

, p. 407 - 409 (2007/10/03)

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.

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