Product Name

  • Name

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

  • EINECS 603-555-2
  • CAS No. 132201-32-2
  • Article Data12
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 222-224 ºC (dec.)
  • Formula C9H12ClNO3
  • Boiling Point 400.3oC at 760 mmHg
  • Molecular Weight 217.652
  • Flash Point 195.9oC
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 132201-32-2 ((2R,3S)-3-Phenylisoserine hydrochloride)
  • Hazard Symbols
  • Synonyms Benzenepropanoicacid, b-amino-a-hydroxy-, hydrochloride, (aR,bS)- (9CI);Benzenepropanoic acid, b-amino-a-hydroxy-, hydrochloride,[R-(R*,S*)]-;(2R,3S)-3-Phenylisoserine hydrochloride;
  • PSA 83.55000
  • LogP 1.63420

Synthetic route

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
132127-34-5

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

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

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

Conditions
ConditionsYield
With hydrogenchloride for 12h; Heating;100%
With hydrogenchloride at 25℃; for 3h;
3-Triisopropylsilyloxy-4-phenylazetidin-2-one
132127-31-2, 132201-31-1

3-Triisopropylsilyloxy-4-phenylazetidin-2-one

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

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

Conditions
ConditionsYield
With hydrogenchloride at 25℃; for 3h;100%
Multi-step reaction with 2 steps
1: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
2: 6N hydrochloric acid / 3 h / 25 °C
View Scheme
(2R,3S)-3-Amino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionic acid isopropyl ester
201339-42-6

(2R,3S)-3-Amino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionic acid isopropyl ester

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

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

Conditions
ConditionsYield
With hydrogenchloride Heating;100%
(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one
132127-31-2

(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one

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

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

Conditions
ConditionsYield
With hydrogenchloride at 25℃; for 5h;98%
Multi-step reaction with 2 steps
1: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
2: 100 percent / 6 N HCl / 12 h / Heating
View Scheme
C16H19NO5

C16H19NO5

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

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

Conditions
ConditionsYield
With hydrogenchloride; water for 5h; Reflux;95%
methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate
122743-18-4

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate

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

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

Conditions
ConditionsYield
Stage #1: methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate With sulfuric acid; acetonitrile at -10 - 20℃;
Stage #2: With hydrogenchloride Heating;		86%
Multi-step reaction with 5 steps
1: p-TsOH / CH2Cl2 / 5 h / Ambient temperature
2: AcBr / CH2Cl2 / 2 h / -15 °C
3: NaN3 / dimethylformamide / 50 °C
4: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature
5: 10percent aq. HCl / 2 h / Heating
View Scheme
Methyl N-acetyl-3-phenylisoserine
158225-44-6

Methyl N-acetyl-3-phenylisoserine

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

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

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;
(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester
195624-97-6

(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester

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

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

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 4h; Yield given;
With hydrogenchloride In water for 4h; Heating;
(2R,3S)-2,3-dihydroxy-3-phenyl-propionic acid
56816-81-0

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

A

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

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

B

(2R,3R)-3-carboxy-2-hydroxy-1-phenylpropanylammonium hydrochloride

(2R,3R)-3-carboxy-2-hydroxy-1-phenylpropanylammonium hydrochloride

Conditions
ConditionsYield
Stage #1: (2R,3S)-2,3-dihydroxy-3-phenyl-propionic acid With sulfuric acid; acetonitrile at -10 - 20℃; for 2h;
Stage #2: With hydrogenchloride for 2h; Heating;
(E)-isopropyl cinnamate
60512-85-8

(E)-isopropyl cinnamate

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL; LiOH
2: HCl / H2O / 4 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / (DHQ)2PHAL, aq. LiOH, K22(OH)4> / 2-methyl-propan-2-ol / 20 h / 4 °C
2: 10percent aq. HCl / 4 h / 100 °C
View Scheme
(E)-N-benzylidene-2-hydroxyaniline
3230-45-3

(E)-N-benzylidene-2-hydroxyaniline

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: (S)-6,6'-dibromo-1,1'-bi-2-naphthol-1,2-dimethylimidazole - Zr(IV) complex / toluene / -78 °C
2: K2CO3
3: cerium ammonium nitrate / methanol
4: 100 percent / 10percent aq. HCl / Heating
View Scheme
Multi-step reaction with 4 steps
1: (R)-6,6'-dibromo-1,1'-bi-2-naphthol-1,2-dimethylimidazole - Zr(IV) complex / toluene / 20 h / -78 °C
2: K2CO3
3: cerium ammonium nitrate / methanol
4: 100 percent / 10percent aq. HCl / Heating
View Scheme
(2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(2-methoxy-phenylamino)-3-phenyl-propionic acid isopropyl ester
201339-46-0

(2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(2-methoxy-phenylamino)-3-phenyl-propionic acid isopropyl ester

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cerium ammonium nitrate / methanol
2: 100 percent / 10percent aq. HCl / Heating
View Scheme
isopropyl 2-tert-butyldimethylsiloxy-3-(2-hydroxyphenyl)amino-3-phenylpropionate
201339-41-5

isopropyl 2-tert-butyldimethylsiloxy-3-(2-hydroxyphenyl)amino-3-phenylpropionate

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: K2CO3
2: cerium ammonium nitrate / methanol
3: 100 percent / 10percent aq. HCl / Heating
View Scheme
Methyl cinnamate
103-26-4

Methyl cinnamate

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

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 71 percent / (DHQ)2PHAL, NMO, K2OsO2(OH)4 / H2O; 2-methyl-propan-2-ol / 23 h / Ambient temperature
2: p-TsOH / CH2Cl2 / 5 h / Ambient temperature
3: AcBr / CH2Cl2 / 2 h / -15 °C
4: NaN3 / dimethylformamide / 50 °C
5: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature
6: 10percent aq. HCl / 2 h / Heating
View Scheme
methyl 2-acetoxy-3-azido-3-phenylpropanoate
158341-43-6

methyl 2-acetoxy-3-azido-3-phenylpropanoate

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature
2: 10percent aq. HCl / 2 h / Heating
View Scheme
methyl (2R,3S)-2-acetoxy-3-bromo-3-phenylpropionate
145987-13-9

methyl (2R,3S)-2-acetoxy-3-bromo-3-phenylpropionate

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaN3 / dimethylformamide / 50 °C
2: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature
3: 10percent aq. HCl / 2 h / Heating
View Scheme
(4R,5S)-2-Methoxy-2-methyl-5-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester
186758-09-8

(4R,5S)-2-Methoxy-2-methyl-5-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: AcBr / CH2Cl2 / 2 h / -15 °C
2: NaN3 / dimethylformamide / 50 °C
3: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature
4: 10percent aq. HCl / 2 h / Heating
View Scheme
N-benzylidene-1,1,1-trimethylsilanamine
17599-61-0

N-benzylidene-1,1,1-trimethylsilanamine

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
2: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
3: 6N hydrochloric acid / 3 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
2: 100 percent / 6N hydrochloric acid / 3 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
2: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
3: 6N hydrochloric acid / 3 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
2: 100 percent / 6N hydrochloric acid / 3 h / 25 °C
View Scheme
benzaldehyde
100-52-7

benzaldehyde

aminoguanidine salt

aminoguanidine salt

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1. hexamethyldisilazane, n-BuLi / 1. THF, hexane, reflux, 3 h; 2. reflux, 2 h
2: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
3: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
4: 6N hydrochloric acid / 3 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: 1. hexamethyldisilazane, n-BuLi / 1. THF, hexane, reflux, 3 h; 2. reflux, 2 h
2: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
3: 100 percent / 6N hydrochloric acid / 3 h / 25 °C
View Scheme
Multi-step reaction with 4 steps
1: 1. hexamethyldisilazane, n-BuLi / 1. THF, hexane, reflux, 3 h; 2. reflux, 2 h
2: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
3: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
4: 6N hydrochloric acid / 3 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: 1. hexamethyldisilazane, n-BuLi / 1. THF, hexane, reflux, 3 h; 2. reflux, 2 h
2: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
3: 100 percent / 6N hydrochloric acid / 3 h / 25 °C
View Scheme
[4-(benzylideneamino)phenyl]methanol
783-08-4

[4-(benzylideneamino)phenyl]methanol

1400

1400

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) LDA / 2.) THF, -95 deg C to -78 deg C
2: cerium ammonium nitrate / tetrahydrofuran
3: 98 percent / 6N hydrochloric acid / 5 h / 25 °C
View Scheme
1-(4-Methoxyphenyl)-3-triisopropylsilyloxy-4-phenyl-2-azetidinone
144465-78-1

1-(4-Methoxyphenyl)-3-triisopropylsilyloxy-4-phenyl-2-azetidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cerium ammonium nitrate / tetrahydrofuran
2: 98 percent / 6N hydrochloric acid / 5 h / 25 °C
View Scheme
(E)-N-benzylidene-1,1,1-trimethylsilanamine
120419-97-8

(E)-N-benzylidene-1,1,1-trimethylsilanamine

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) LDA / 2a) THF, -78 deg C, 4 h, 2b) rt, overnight
2: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
3: 100 percent / 6 N HCl / 12 h / Heating
View Scheme
(2R,3S)-3-amino-2-hydroxy-3-phenylpropionic acid ethyl ester
143615-00-3

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

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

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

Conditions
ConditionsYield
With hydrogenchloride; water Heating;
C12H13NO4

C12H13NO4

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Burkholderia cepacia lipase / di-isopropyl ether / 0.08 h / 50 °C / Resolution of racemate; Enzymatic reaction
2: hydrogenchloride; water / 5 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: Burkholderia cepacia lipase / toluene / 0.08 h / 50 °C / Resolution of racemate; Enzymatic reaction
2: hydrogenchloride; water / 5 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: Burkholderia cepacia lipase / di-isopropyl ether / 0.5 h / 25 °C / Enzymatic reaction
2: hydrogenchloride; water / 5 h / Reflux
View Scheme
cis-rac-3-acetoxy-4-phenylazetidin-2-one

cis-rac-3-acetoxy-4-phenylazetidin-2-one

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Sonication
2: Burkholderia cepacia lipase / di-isopropyl ether / 0.08 h / 50 °C / Resolution of racemate; Enzymatic reaction
3: hydrogenchloride; water / 5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: Sonication
2: Burkholderia cepacia lipase / toluene / 0.08 h / 50 °C / Resolution of racemate; Enzymatic reaction
3: hydrogenchloride; water / 5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: Sonication
2: Burkholderia cepacia lipase / di-isopropyl ether / 0.5 h / 25 °C / Enzymatic reaction
3: hydrogenchloride; water / 5 h / Reflux
View Scheme
3-Phenylpropenol
104-54-1

3-Phenylpropenol

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: D-(-)-diisopropyl tartrate; titanium(IV)isopropoxide / dichloromethane / Molecular sieve
2: sulfuric acid / 8 h / 20 - 25 °C
3: dipyridine chromium(VI) oxide / dichloromethane / 10 °C
4: hydrogenchloride / water / 100 - 110 °C
View Scheme
(2S,3S)-2,3-epoxy-3-phenyl-1-propanol
104196-23-8

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / 8 h / 20 - 25 °C
2: dipyridine chromium(VI) oxide / dichloromethane / 10 °C
3: hydrogenchloride / water / 100 - 110 °C
View Scheme
C11H11NO3

C11H11NO3

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

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

Conditions
ConditionsYield
With hydrogenchloride In water at 100 - 110℃;
methanol
67-56-1

methanol

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

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

methyl (2R,3S)-3-phenylisoserinate hydrochloride

methyl (2R,3S)-3-phenylisoserinate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0℃; for 3h;100%
With thionyl chloride at 0℃;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

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

RPR 130523
145514-62-1

RPR 130523

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone89%
With triethylamine In tetrahydrofuran; water at 0 - 20℃;
With sodium hydroxide In tetrahydrofuran
methanol
67-56-1

methanol

benzoyl chloride
98-88-4

benzoyl chloride

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

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

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

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

Conditions
ConditionsYield
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
benzoyl chloride
98-88-4

benzoyl chloride

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

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

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

(2R,3S)-N-benzoyl-3-phenylisoserine

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water for 16h; Ambient temperature;72%
With sodium hydrogencarbonate In dichloromethane; water70%
With sodium hydroxide for 3h; Ambient temperature; Yield given;
methanol
67-56-1

methanol

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

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

methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate
124605-42-1

methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; (2R,3S)-3-phenylisoserine hydrochloride With sodium hydroxide In tetrahydrofuran; water at 20 - 40℃; for 4h;
Stage #2: methanol		60%
...Expand
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

orthobenzoic acid trimethyl ester
707-07-3

orthobenzoic acid trimethyl ester

(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 toluene for 8h; Heating;41%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

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

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

benzyl alcohol
100-51-6

benzyl alcohol

(2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid benzyl ester; compound with toluene-4-sulfonic acid

(2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid benzyl ester; compound with toluene-4-sulfonic acid

Conditions
ConditionsYield
In benzene for 10h; Heating;1600 mg
...Expand
succinimidyl 2,2,2-trichloroethyl carbonate
66065-85-8

succinimidyl 2,2,2-trichloroethyl carbonate

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

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

(2R,3S)-2-Hydroxy-3-phenyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid

(2R,3S)-2-Hydroxy-3-phenyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane at 20℃; for 1h;
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

benzyl chloroformate
501-53-1

benzyl chloroformate

(2R,3S)-3-Benzyloxycarbonylamino-2-hydroxy-3-phenyl-propionic acid

(2R,3S)-3-Benzyloxycarbonylamino-2-hydroxy-3-phenyl-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether at 0 - 20℃;
With sodium hydroxide In 1,4-dioxane at 0℃; for 3h;
methanol
67-56-1

methanol

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

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

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

(2R,3S)-3-phenylisoserine methyl ester

Conditions
ConditionsYield
With thionyl chloride at 20℃;
With thionyl chloride at 20℃; for 6h; Time; Cooling with ice;
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

(4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-benzyl ester

(4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: SOCl2 / 20 °C
2: aq. NaHCO3 / CH2Cl2 / 3 h / 20 °C
3: 469 mg / pyridinium p-toluenesulfonate / toluene / Heating
4: aq. KOH / methanol / 2 h / 20 °C
View Scheme
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

(4S,5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-benzyloxycarbonyl-1,3-oxazolidine

(4S,5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-benzyloxycarbonyl-1,3-oxazolidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 20 °C
2: aq. NaHCO3 / CH2Cl2 / 3 h / 20 °C
3: 469 mg / pyridinium p-toluenesulfonate / toluene / Heating
View Scheme
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

2'-O-tert-butoxycarbonyl-3'-N-de(tert-butoxycarbonyl)docetaxel

2'-O-tert-butoxycarbonyl-3'-N-de(tert-butoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: SOCl2 / 20 °C
2.1: aq. NaHCO3 / CH2Cl2 / 3 h / 20 °C
3.1: 469 mg / pyridinium p-toluenesulfonate / toluene / Heating
4.1: aq. KOH / methanol / 2 h / 20 °C
5.1: DMAP; DCC / CH2Cl2 / 2 h / 20 °C
5.2: 80 percent / p-toluenesulfonic acid / methanol / 5 h / 20 °C
6.1: 84 percent / pyridine; DMAP / CH2Cl2 / 20 °C
7.1: H2 / Pd/C / ethyl acetate / 8 h / 20 °C
View Scheme
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III
850933-54-9

13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: SOCl2 / 20 °C
2.1: aq. NaHCO3 / CH2Cl2 / 3 h / 20 °C
3.1: 469 mg / pyridinium p-toluenesulfonate / toluene / Heating
4.1: aq. KOH / methanol / 2 h / 20 °C
5.1: DMAP; DCC / CH2Cl2 / 2 h / 20 °C
5.2: 80 percent / p-toluenesulfonic acid / methanol / 5 h / 20 °C
View Scheme
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

13-(3'-N-benzyloxycarbonyl-2'-tert-butoxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III
850933-55-0

13-(3'-N-benzyloxycarbonyl-2'-tert-butoxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: SOCl2 / 20 °C
2.1: aq. NaHCO3 / CH2Cl2 / 3 h / 20 °C
3.1: 469 mg / pyridinium p-toluenesulfonate / toluene / Heating
4.1: aq. KOH / methanol / 2 h / 20 °C
5.1: DMAP; DCC / CH2Cl2 / 2 h / 20 °C
5.2: 80 percent / p-toluenesulfonic acid / methanol / 5 h / 20 °C
6.1: 84 percent / pyridine; DMAP / CH2Cl2 / 20 °C
View Scheme
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

C70H69NO19

C70H69NO19

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: SOCl2 / 20 °C
2.1: aq. NaHCO3 / CH2Cl2 / 3 h / 20 °C
3.1: 469 mg / pyridinium p-toluenesulfonate / toluene / Heating
4.1: aq. KOH / methanol / 2 h / 20 °C
5.1: DMAP; DCC / CH2Cl2 / 2 h / 20 °C
5.2: p-toluenesulfonic acid / methanol / 5 h / 20 °C
View Scheme
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate
133524-69-3, 133577-36-3, 133577-37-4

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: SOCl2 / 20 °C
2.1: aq. NaHCO3 / CH2Cl2 / 3 h / 20 °C
3.1: 469 mg / pyridinium p-toluenesulfonate / toluene / Heating
4.1: aq. KOH / methanol / 2 h / 20 °C
5.1: DMAP; DCC / CH2Cl2 / 2 h / 20 °C
5.2: 80 percent / p-toluenesulfonic acid / methanol / 5 h / 20 °C
6.1: H2 / Pd/C / ethyl acetate / 8 h / 20 °C
View Scheme
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

(-)-(2R,3S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate
158810-74-3

(-)-(2R,3S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 20 °C
2: aq. NaHCO3 / CH2Cl2 / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 100 percent / SOCl2 / 0 °C
2: NaHCO3
View Scheme
Multi-step reaction with 2 steps
1: 100 percent / SOCl2 / 3 h / 0 °C
2: 86 percent / NaHCO3 / CH2Cl2 / 2 h
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / 1,4-dioxane / 3 h / 0 °C
2: N,N-dimethyl-formamide; thionyl chloride / 12 h / -78 - 20 °C
View Scheme
(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
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

(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
Multi-step reaction with 3 steps
1: NaOH / H2O
2: DCC; DMAP / CH2Cl2 / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 41 percent / toluene / 8 h / Heating
2: 86 percent / NaOH / methanol; H2O / 20 °C
3: dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 20 °C
View Scheme
(2R,3S)-3-phenylisoserine hydrochloride
132201-32-2

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

(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
395664-47-8

(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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaOH / H2O
2: DCC; DMAP / CH2Cl2 / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 41 percent / toluene / 8 h / Heating
2: 86 percent / NaOH / methanol; H2O / 20 °C
3: dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 20 °C
View Scheme

(2R,3S)-3-Phenylisoserine hydrochloride Specification

The CAS registry number of (2R,3S)-3-Phenylisoserine hydrochloride is 132201-32-2. It is also called Benzenepropanoic acid, b-amino-a-hydroxy-,hydrochloride (1:1), (aR,bS)-. The IUPAC name is 3-amino-2-hydroxy-3-phenylpropanoic acid hydrochloride (1:1). In addition, the molecula formula is C9H12ClNO3 and the molecular weight is 217.6495. It should be stored in a cool environment.

Physical properties about this chemical are: (1)ACD/LogP: 0.95; (2)# of Rule of 5 Violations: 0 ; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 4; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 83.55 Å2 ; (11)Flash Point: 208.5 °C; (12)Enthalpy of Vaporization: 71.17 kJ/mol; (13)Boiling Point: 421.1 °C at 760 mmHg; (14)Vapour Pressure: 7.63E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.NC(C(O)C(O)=O)c1ccccc1
(2)InChI: InChI=1/C9H11NO3.ClH/c10-7(8(11)9(12)13)6-4-2-1-3-5-6;/h1-5,7-8,11H,10H2,(H,12,13);1H
(3)InChIKey: OTJZSGZNPDLQAJ-UHFFFAOYAA

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