132201-32-2

Basic information

• Product Name: (2R,3S)-3-Phenylisoserine hydrochloride
• Synonyms: (2R,3S)-3-Amino-2-hydroxy-3-phenyl-propanoic acid hydrochloride;(2r,3s)-3-phenylisoserine hydrochloride;(2R,3S)-3-PHENYLISOSERINE HCl;(2R,3S)-3-phenylisoserine.HCl;(2R,3S)-Phenylisoserine hydrochloride;(2R,3S)-3-phenylisoserine Hydrochloride ( Paclitaxel side chain);(2R,3S)-3-PHENYLISOSERINE HYDROCHLORIDE,98+%;3-(2R,3S)-PHENYLISOSERINE HCL
• CAS NO: 132201-32-2
• Molecular Formula: C₉H₁₁NO₃*ClH
• Molecular Weight: 217.65
• EINECS: 1806241-263-5
• Mol File: 132201-32-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 222-224°C (dec.)
• Boiling Point: 400.3oC at 760 mmHg
• Flash Point: 195.9oC
• Appearance: /
• Vapor Pressure: 3.98E-07mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (2R,3S)-3-Phenylisoserine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-Phenylisoserine hydrochloride(132201-32-2)
• EPA Substance Registry System: (2R,3S)-3-Phenylisoserine hydrochloride(132201-32-2)

Safety Data

• Hazardous Substances Data: 132201-32-2(Hazardous Substances Data)

Usage

Uses

(2R,3S)-3-Phenylisoserine Hydrochloride is used in the synthetic preparation of the catalytic asymmetric synthesis of both syn- and anti-β-amino alcohols. (2R,3S)-3-Phenylisoserine Hydrochloride is also used for the synthesis of N-benzoylphenylisoserinates of Lactarius sesquiterpenoid alcohols and is responsible for their antifeedant properties against storage pests.

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/t7-,8+;/m0./s1

Synthetic route

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5) → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2)

Conditions	Yield
With hydrogenchloride for 12h; Heating;	100%
With hydrogenchloride at 25℃; for 3h;

3-Triisopropylsilyloxy-4-phenylazetidin-2-one (132127-31-2, 132201-31-1) → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2)

Conditions	Yield
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-phenylisoserine hydrochloride (132201-32-2)

Conditions	Yield
With hydrogenchloride Heating;	100%

(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one (132127-31-2) → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2)

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

Conditions	Yield
With hydrogenchloride; water for 5h; Reflux;	95%

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate (122743-18-4) → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2)

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

Conditions	Yield
With hydrogenchloride for 2h; Heating;

(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester (195624-97-6) → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2)

Conditions	Yield
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)-3-phenylisoserine hydrochloride (132201-32-2) + (2R,3R)-3-carboxy-2-hydroxy-1-phenylpropanylammonium hydrochloride

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

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

Conditions	Yield
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)-3-phenylisoserine hydrochloride (132201-32-2)

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

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

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

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

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

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

Conditions	Yield
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) + aminoguanidine salt → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2)

Conditions	Yield
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) + 1400 → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2)

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

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

Conditions	Yield
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-phenylisoserine hydrochloride (132201-32-2)

Conditions	Yield
With hydrogenchloride; water Heating;

C12H13NO4 → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2)

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

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

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

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

Conditions	Yield
With hydrogenchloride In water at 100 - 110℃;

methanol (67-56-1) + (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → methyl (2R,3S)-3-phenylisoserinate hydrochloride

Conditions	Yield
With thionyl chloride at 0℃; for 3h;	100%
With thionyl chloride at 0℃;	100%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → RPR 130523 (145514-62-1)

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	89%
With triethylamine In tetrahydrofuran; water at 0 - 20℃;
With sodium hydroxide In tetrahydrofuran

methanol (67-56-1) + benzoyl chloride (98-88-4) + (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4)

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%

benzoyl chloride (98-88-4) + (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → (2R,3S)-N-benzoyl-3-phenylisoserine (132201-33-3)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water for 16h; Ambient temperature;	72%
With sodium hydrogencarbonate In dichloromethane; water	70%
With sodium hydroxide for 3h; Ambient temperature; Yield given;

methanol (67-56-1) + di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate (124605-42-1)

Conditions	Yield
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%

(2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) + orthobenzoic acid trimethyl ester (707-07-3) → (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester (146848-91-1)

Conditions	Yield
In toluene for 8h; Heating;	41%

toluene-4-sulfonic acid (104-15-4) + (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) + benzyl alcohol (100-51-6) → (2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid benzyl ester; compound with toluene-4-sulfonic acid

Conditions	Yield
In benzene for 10h; Heating;	1600 mg

succinimidyl 2,2,2-trichloroethyl carbonate (66065-85-8) + (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → (2R,3S)-2-Hydroxy-3-phenyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid

Conditions	Yield
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane at 20℃; for 1h;

(2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) + benzyl chloroformate (501-53-1) → (2R,3S)-3-Benzyloxycarbonylamino-2-hydroxy-3-phenyl-propionic acid

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

methanol (67-56-1) + (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → (2R,3S)-3-phenylisoserine methyl ester (157240-36-3)

Conditions	Yield
With thionyl chloride at 20℃;
With thionyl chloride at 20℃; for 6h; Time; Cooling with ice;

(2R,3S)-3-phenylisoserine hydrochloride (132201-32-2) → (4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-benzyl ester

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

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

Conditions

Yield

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

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

Conditions	Yield
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) → C70H69NO19

Conditions	Yield
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) → (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)

Conditions	Yield
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)-methyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate (158810-74-3)

Conditions	Yield
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) → (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

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

Conditions	Yield
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

Upstream product

• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 104-54-1 3-Phenylpropenol 
• 133066-59-8 cis-rac-3-acetoxy-4-phenylazetidin-2-one 
• 144465-78-1 1-(4-Methoxyphenyl)-3-triisopropylsilyloxy-4-phenyl-2-azetidinone 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 100-52-7 benzaldehyde 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 186758-09-8 (4R,5S)-2-Methoxy-2-methyl-5-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 145987-13-9 methyl (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionate 
• 158341-43-6 methyl 2-acetoxy-3-azido-3-phenylpropanoate 
• 103-26-4 Methyl cinnamate 
• 201339-41-5 isopropyl 2-tert-butyldimethylsiloxy-3-(2-hydroxyphenyl)amino-3-phenylpropionate 

Downstream Products

• 655228-33-4 (2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid cyclohexyl ester 
• 655228-34-5 Isobutyric acid (1R,2S)-2-tert-butoxycarbonylamino-1-carboxy-2-phenyl-ethyl ester 
• 787547-61-9 (2R,3S)-3-Amino-2-tert-butoxycarbonyloxy-3-phenyl-propionic acid cyclohexyl ester 
• 655228-28-7 (2R,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonyloxy-3-phenyl-propionic acid 
• 655228-35-6 Isobutyric acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyclohexyloxycarbonyl-2-phenyl-ethyl ester 
• 655228-31-2 (2R,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonyloxy-3-phenyl-propionic acid cyclohexyl ester 
• 602319-10-8 (2R,4S,5R)-5-carboxy-2-(4-methoxyphenyl)-4-phenyl-3-Troc-1,3-oxazolidine 
• 602319-09-5 (2R,4S,5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-Troc-1,3-oxazolidine 
• 307923-51-9 2'-O-benzoyl-3'-N-debenzoyl-paclitaxel 
• 602319-12-0 3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel 
• 602319-13-1 2'-O-benzoyl-3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel 
• 602319-11-9 C₅₄H₅₅Cl₆NO₁₈ 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 155396-65-9 (2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid 

Relevant articles and documents

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 method of phenyl isoserine hydrochloride and intermediate thereof (by machine translation)

The invention provides a method .for synthesizing phenyl isoserine hydrochloride and an intermediate thereof, II of the compound shown in formula, in the presence of a catalyst: and the method comprises the following steps, synthesizing paclitaxel and docetaxel in the following steps: synthesizing paclitaxel and docetaxel as shown in the following reaction I as shown, in the following steps: II, synthesizing paclitaxel and docetaxel in a low price . and synthesizing the paclitaxel and docetaxel in an inexpensive manner . The invention provides cheap chiral side chain raw material, for synthesizing paclitaxel and, docetaxel as shown in the following step: [,] The present invention provides cheap chiral side. chain raw materials. (by machine translation)

Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.