Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate supplier

Name
Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate
EINECS 608-809-6
CAS No. 32981-85-4
Article Data55
CAS DataBase
Density 1.236 g/cm³
Solubility
Melting Point 178-183℃
Formula C₁₇H₁₇NO₄
Boiling Point 540.3 °C at 760 mmHg
Molecular Weight 299.326
Flash Point 280.6 °C
Transport Information
Appearance White crystal
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms PACLITAXEL SIDE CHAIN 4;PACLITAXEL SIDE CHAIN NO 4;C-13 SIDE CHAIN FOR PACLITAXEL II;(2R,3S)-1-Benzoyl-2-Hydroxy-3-Aminophenylpionic Acid Ester;METHYL (2R,3S)-3-BENZAMIDO-2-HYDRO-3-PHENYLPROPIONATE;METHYL (2R,3S)-3-BENZAMIDO-2-HYDROXY-3-PHENYLPROPIONATE;N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE METHYL ESTER;PACLITAXE SIDE CHIAN 4
PSA 75.63000
LogP 2.08250

Synthetic route

: 145041-37-8
methyl (2R,3S)-3-benzoylamino-2-benzyloxy-3-phenylpropanethioate

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol under 4654.46 Torr;	100%
With hydrogen; 1% Pd/C In methanol under 4654.46 Torr;	100%
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 60℃; for 1h;	78%
With hydrogen; palladium on activated charcoal In ethanol at 60℃;	78%

: 99458-15-8
Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate

: 98-88-4
benzoyl chloride

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
Stage #1: Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate; benzoyl chloride With dmap; triethylamine In ethyl acetate at 20℃; for 4h; Stage #2: With hydrogen; palladium on activated charcoal In methanol; ethyl acetate for 48h; Further stages.;	92%
Stage #1: Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate; benzoyl chloride With dmap; triethylamine In methanol; ethyl acetate at 20℃; for 7h; Stage #2: With hydrogen; palladium on activated carbon In methanol; ethyl acetate for 48h;	92%
Stage #1: Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate; benzoyl chloride; dmap In methanol; ethyl acetate at 20℃; for 7h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol; ethyl acetate for 48h;	88%

: 146848-86-4
methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h;	92%

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

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;	90%
With hydrogenchloride In methanol for 5h; Heating;	85%
With hydrogenchloride In methanol for 5h; Heating;	85%

: 186581-53-3, 908094-01-9
diazomethane

: 132201-33-3
(2R,3S)-N-benzoyl-3-phenylisoserine

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether	90%
In methanol; diethyl ether

: 99458-16-9
(2R,3S)-(+)-methyl 3-azido-2-benzoly-3-phenylpropionate

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol	88%
With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal	76%
With hydrogen; palladium on activated charcoal In methanol under 2585.7 Torr; for 4h;	74%
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 760 Torr; for 48h;	71%
With hydrogen; palladium on activated charcoal 1.) CH3OH, 15 h, 2.) CH3OH, RT, 72 h; Yield given. Multistep reaction;

: 67-56-1
methanol

: 98-88-4
benzoyl chloride

: 195624-97-6
(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
Stage #1: methanol; (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester With hydrogenchloride for 20h; Heating; Stage #2: benzoyl chloride With triethylamine In dichloromethane at 0 - 20℃;	88%

...Expand

: 67-56-1
methanol

: 98-88-4
benzoyl chloride

: 132201-32-2
(2R,3S)-3-phenylisoserine hydrochloride

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
Stage #1: benzoyl chloride; (2R,3S)-3-phenylisoserine hydrochloride With sodium hydroxide In water at 20℃; for 1h; pH=9 - 12; Stage #2: methanol Concentration;	85.6%

...Expand

: 67-56-1
methanol

: 100-44-7
benzyl chloride

: 195624-97-6
(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
Stage #1: methanol; (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester With hydrogenchloride for 20h; Addition; Heating; Stage #2: benzyl chloride With triethylamine In dichloromethane at 0 - 20℃; for 2h; Substitution; Further stages.;	85%

...Expand

: 144541-45-7
methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane for 5h; Inert atmosphere; Reflux;	85%
Multi-step reaction with 2 steps 1.1: SOCl2 / CH2Cl2 / Heating 2.1: HCl / H2O; methanol / Heating 2.2: NaHCO3 / H2O; methanol / 50 °C View Scheme
Multi-step reaction with 2 steps 1: 90 percent / DEAD; PPh3 / benzene / 20 h / 20 °C 2: 90 percent / 1N aq. HCl / methanol / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 77 percent / Ph3P, diethylazodicarboxylate / tetrahydrofuran / Ambient temperature 2: 1.) aq. HCl, 2.) aq. NaHCO3 / 1) CH3OH, room temperature, 1.5 h; 2) room temperature, 16 h View Scheme
Multi-step reaction with 2 steps 1: 1) SOCl2 / 1) CHCl3, 45 deg C, 5 h, 2) CHCl3, reflux, 48 h 2: 80 percent / 1N HCl / methanol / 2 h / Heating View Scheme

: 67-56-1
methanol

: 222727-06-2
S-Ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanethioate

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With silver trifluoroacetate Ambient temperature;	84%
With silver trifluoroacetate at 20℃; for 1h; Methylation;	84%

: 33069-62-4
taxol

A: 32981-86-5
10-deacetylbaccatin III

B: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

C: 71629-92-0
10-deacetyl-7-epi-baccatin III

Conditions

Conditions	Yield
With lithium iodide In methanol for 10h; Ambient temperature;	A 58% B 82% C 40%
With lithium iodide In methanol for 10h; Ambient temperature;	A 58% B 82% C 40%

...Expand

: 105454-04-4
7-epipaclitaxel

A: 31077-81-3
7-epi-baccatin III

B: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

C: 71629-92-0
10-deacetyl-7-epi-baccatin III

Conditions

Conditions	Yield
With lithium iodide In methanol for 14h; Ambient temperature;	A 56% B 78% C 17%

...Expand

: 148930-54-5
(2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-9-({(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl}oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9, 10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

A: 32981-86-5
10-deacetylbaccatin III

B: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

C: 71629-92-0
10-deacetyl-7-epi-baccatin III

Conditions

Conditions	Yield
With lithium iodide In methanol Ambient temperature; 2 weeks;	A 22% B 71% C 34%

...Expand

: 67-56-1
methanol

: isobutyl (4S,5R)-3-benzoyl-4-phenyloxazolidin-2-one-5-carboxylate

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 1.5h;	51%

: 67-56-1
methanol

: 3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid (1R,2R,3R,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester

A: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

B: 135821-94-2
methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
In methanol Title compound not separated from byproducts;
With sodium methylate Title compound not separated from byproducts;

...Expand

: 67-56-1
methanol

: 3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

A: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

B: 503178-23-2
3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid methyl ester

C: 135821-94-2
methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
In methanol Title compound not separated from byproducts;
With sodium methylate Title compound not separated from byproducts;

...Expand

: 67-56-1
methanol

: 3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid (1R,2S)-2-phenyl-cyclohexyl ester

A: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

B: 503178-23-2
3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid methyl ester

C: 135821-94-2
methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
In methanol Title compound not separated from byproducts;
With sodium methylate Title compound not separated from byproducts;

...Expand

: 67-56-1
methanol

: 3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

A: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

B: 503178-23-2
3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid methyl ester

Conditions

Conditions	Yield
In methanol Title compound not separated from byproducts;
With sodium methylate

...Expand

: 67-56-1
methanol

: 3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

A: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

B: 503178-23-2
3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid methyl ester

C: 135821-94-2
methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With sodium methylate Title compound not separated from byproducts;

...Expand

: 124-41-4
sodium methylate

: (+)-cis-1-benzoyl-3-acetoxy-4-phenylazetidin-2-one

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
In methanol at 25℃; for 1h;	79 mg

: 98-88-4
benzoyl chloride

: 157240-36-3
(2R,3S)-3-phenylisoserine methyl ester

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
Yield given;
With sodium hydrogencarbonate In ethyl acetate
With sodium hydrogencarbonate In tetrahydrofuran; water at 0℃; for 2h;	0.123 g
With triethylamine
In dichloromethane at 20℃; for 5h; Time; Cooling with ice;	267 g

: 98-88-4
benzoyl chloride

: 147058-27-3
methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With sodium hydroxide; hydrogen; palladium on activated charcoal 1.) MeOH, room temp., 30 h, 2.) THF, water, 0 deg C, 30 min; Yield given. Multistep reaction;

: taxol

A: 93-58-3
benzoic acid methyl ester

B: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

C: 7-epi-10-deacetyltaxol

D: 10-deacetyltaxol

Conditions

Conditions	Yield
With hydrogenchloride In methanol Ambient temperature;

...Expand

: taxol

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With ammonium hydroxide In methanol Ambient temperature;
With alkaline solution

: 144494-74-6
(R)-3-benzamido-3-phenylpropanoic acid methyl ester

A: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

B: 144541-45-7
methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine; lithium chloride; lithium diisopropyl amide 1) -42 deg C, 2) -100 to -78 deg C; Yield given. Multistep reaction. Yields of byproduct given;
With MoO5pyridineHMPA; potassium hexamethylsilazane 1.) toluene, THF, -78 deg C to -25 deg C; 2.) toluene, THF, -60 deg C, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

: Benzoic acid (R)-2-azido-1-methoxycarbonyl-2-phenyl-ethyl ester

A: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

B: 151764-53-3
(2R,3R)-(-)-2-hydroxy-3-(benzoylamino)-3-phenylpropanoic acid methyl ester

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol
With hydrogen; palladium on activated charcoal In methanol Title compound not separated from byproducts;

: 157722-43-5
(2R,3S)-3-Benzoylamino-3-phenyl-2-trimethylsilanyloxy-propionic acid methyl ester

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions

Conditions	Yield
With potassium fluoride In water

: 32981-85-4, 132074-01-2, 135821-94-2, 144541-45-7
syn-(+/-)-2-hydroxy-3-(benzoylamino)-3-phenylpropanoic acid methyl ester

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 67-56-1
methanol

: 33069-62-4
taxol

A: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

B: 27548-93-2
baccatin III

C: 105454-04-4
7-epipaclitaxel

Conditions

Conditions	Yield
at 58 - 116℃; Thermodynamic data; apparent activation energy Ea, other solvents, temperatures;

...Expand

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 99458-19-2
(2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 40h;	96%

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 124-63-0
methanesulfonyl chloride

: 274681-89-9
(2R,3S)-3-benzoylamino-2-methanesulfonyloxy-3-phenylpropanoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	93%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1.5h; Mesylation;	86%

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 157826-09-0
Methyl (2R,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In cyclohexane; toluene	91%

: 1515-81-7
1-methoxy-4-(methoxymethyl)benzene

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 157826-09-0
Methyl (2R,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile Heating;	90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 60℃;	69%

: 116-11-0
2-Methoxypropene

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 202390-84-9
Methyl (4S,5R)-3-benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In toluene at 85℃;	89%
With pyridinium p-toluenesulfonate In toluene at 80℃; for 10h; Etherification; Cyclization;	89%
With toluene-4-sulfonic acid at 80℃;

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 227962-26-7
(4S,5S)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester

Conditions

Conditions	Yield
With dmap; trifluoromethylsulfonic anhydride In dichloromethane at -30℃; for 1h;	85%
With dmap; trifluoromethylsulfonic anhydride In dichloromethane at -30℃; for 1h; Cyclization; Dehydration;	84%
With dmap; sulfuryl dichloride In dichloromethane at 0℃; Cyclization;	65%
Multi-step reaction with 2 steps 1: 93 percent / Et3N / tetrahydrofuran / 0 - 20 °C 2: DBU / CHCl3 / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 86 percent / Et3N / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: DBU / CHCl3 / 2 h / Heating View Scheme

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 107-30-2
chloromethyl methyl ether

: 99458-17-0
(2R,3S)-N-benzoyl-O-(methoxymethyl)-3-phenylisoserine methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 40h;	82%

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 132201-33-3
(2R,3S)-N-benzoyl-3-phenylisoserine

Conditions

Conditions	Yield
With potassium carbonate In methanol at 23℃; for 12h;	80%

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 202390-85-0
Methyl (2S,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In toluene	79%

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

A: 202390-85-0
Methyl (2S,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

B: 157826-09-0
Methyl (2R,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In toluene at 130℃; Cycloaddition;	A 79% B 18%

...Expand

: 3587-60-8
Benzyloxymethyl chloride

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 99458-18-1
(2R,3S)-N-benzoyl-O-<(benzyloxy)methyl>-3-phenylisoserine methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 40h;	75%

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: 150-78-7
1,4-dimethoxybezene

: 157826-09-0
Methyl (2R,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 70℃; for 0.116667h; Substitution; Cyclization;	75%

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

: (4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions

Conditions	Yield
Stage #1: p-Anisaldehyde dimethyl acetal; methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate With pyridinium p-toluenesulfonate In toluene for 6h; Inert atmosphere; Reflux; Stage #2: With methanol; sodium hydroxide In tetrahydrofuran at 0 - 25℃; for 3h;	75%

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

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

B: 235432-33-4
3-N-benzoyl-4-phenyl-(4S,5R)-2-oxo-1,2,3-oxathiazolidine methyl ester

C: 235432-34-5
3-N-benzoyl-4-phenyl-(4S,5R)-2-oxo-1,2,3-oxathiazolidine methyl ester

Conditions

Conditions	Yield
With thionyl chloride; triethylamine In benzene at 0 - 5℃; for 0.25h; Cyclization;	A 3% B 68% C 14%

...Expand

: 91352-76-0
2,4-dimethoxybenzaldehyde dimethylacetal

: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

A: methyl-(4S,5R)-N-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidine carboxylate

B: methyl-(4S,5R)-N-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidine carboxylate

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In tetrahydrofuran at 100℃; for 1.5h; Condensation; Title compound not separated from byproducts;	A 64% B n/a

...Expand

Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate Specification

The CAS registry number of Benzenepropanoicacid, b-(benzoylamino)-a-hydroxy-, methyl ester, (aR,bS)- is 32981-85-4. The IUPAC name is methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate. In addition, the molecula formula is C₁₇H₁₇NO₄ and the molecular weight is 299.32. It belongs to the classes of Chiral Chemicals and Intermediates. It is a kind of white crystal powder.

Physical properties about Benzenepropanoicacid, b-(benzoylamino)-a-hydroxy-, methyl ester, (aR,bS)- are: (1)ACD/LogP: 2.90; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.9; (4)ACD/LogD (pH 7.4): 2.9; (5)ACD/BCF (pH 5.5): 94.35; (6)ACD/BCF (pH 7.4): 94.34; (7)ACD/KOC (pH 5.5): 901.82; (8)ACD/KOC (pH 7.4): 901.8; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 55.84 Å²; (13)Index of Refraction: 1.588; (14)Molar Refractivity: 81.53 cm³; (15)Molar Volume: 242.1 cm³; (16)Polarizability: 32.32 ×10^-24cm³; (17)Surface Tension: 51.7 dyne/cm; (18)Density: 1.236 g/cm³; (19)Flash Point: 280.6 °C; (20)Enthalpy of Vaporization: 86.08 kJ/mol; (21)Boiling Point: 540.3 °C at 760 mmHg; (22)Vapour Pressure: 1.66E-12 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)[C@H](O)[C@@H](NC(=O)c1ccccc1)c2ccccc2
(2)InChI: InChI=1/C17H17NO4/c1-22-17(21)15(19)14(12-8-4-2-5-9-12)18-16(20)13-10-6-3-7-11-13/h2-11,14-15,19H,1H3,(H,18,20)/t14-,15+/m0/s1
(3)InChIKey: UYJLJICUXJPKTB-LSDHHAIUBE

Product Name

Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate

Synthetic route

Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate Specification

Related Products

Hot Products