28143-91-1

Basic information

• Product Name: (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol
• Synonyms: S-BASE;LBS;Levo-Amin-odiol;threo-2-amino-1-phenyl-1,3-propanediol;L(+)-THREO-2-AMINO-1-PHENYL-1,1,3-PROPANEDIOL;L-(+)-THREO-2-AMINO-1-PHENYL-1,3-PROPANEDIOL;L-THREO-(+)-PHENYL-2-AMINO-1,3-PROPANDIOL;L-(+)-THREO-1-PHENYL-2-AMINO-1,3-PROPANEDIOL
• CAS NO: 28143-91-1
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.21
• EINECS: 248-867-6
• Product Categories: Propanes/propenes;chiral;Amino Alcohols (Chiral);Chiral Building Blocks;Asymmetric Synthesis;for Resolution of Acids;Optical Resolution;Synthetic Organic Chemistry
• Mol File: 28143-91-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 295.79°C (rough estimate)
• Flash Point: 171.9 °C
• Appearance: White to yellow/Crystals or Crystalline Powder
• Density: 1.1222 (rough estimate)
• Vapor Pressure: 7.87E-06mmHg at 25°C
• Refractive Index: 26.5 ° (C=1, MeOH)
• Storage Temp.: 2-8°C
• PKA: 11.73±0.45(Predicted)
• BRN: 2804071
• CAS DataBase Reference: (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol(28143-91-1)
• EPA Substance Registry System: (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol(28143-91-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 28143-91-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 28143-91-1 differently. You can refer to the following data:
1. (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol is a compound belonging to the chiral amino alchohol group which are used as emulsifying agents in dry-cleaning soaps, wax removers, cosmetics, paints and insecticides. (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol is used in the preparation of potential anticancer agents
2. Asymetric synthesis of chiral 2-oxazolines
3. Precursor to chiral 2-oxazolines. Auxiliary for the preparation of chiral 2-oxazolines from carboxylic acid derivatives.

InChI:InChI=1/C9H13NO2/c10-8(6-11)9(12)7-4-2-1-3-5-7/h1-5,8-9,11-12H,6,10H2/t8-,9+/m0/s1

Synthetic route

(2R,3S)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester (119677-35-9) → (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

(+/-)-threo-2-amino-1-phenyl-1,3-propanediol (3306-06-7, 5285-86-9, 28143-91-1, 36391-67-0, 36391-68-1, 46032-98-8, 55057-81-3, 105452-39-9, 119364-52-2) → (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1)

Conditions	Yield
With L-Tartaric acid
With L-(-)-O,O'-dibenzoyltartaric acid
With (1S)-(+)-3-bromocamphor-10-sulfonic acid
With D-Glutamic acid

1-Phenyl-2-acetamido-1,3-propandiol (91247-54-0) → (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + (1R,2R)-2-amino-1-phenylpropane-1,3-diol (46032-98-8) + (1R,2S)-(+)-2-amino-1-phenyl-1,3-propanediol (105452-39-9) + (1S,2R)-2-amino-1-phenylpropane-1,3-diol (119364-52-2)

Conditions	Yield
hydrolysis;

((1S,2S)-2-Hydroxy-1-hydroxymethyl-2-phenyl-ethyl)-carbamic acid 2-(4-methoxy-phenyl)-2-oxo-ethyl ester (125219-10-5) → (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Conditions	Yield
Irradiation; mild conditions;

(1S,2S)-2-amino-1-<4-amino-phenyl>-propane-1,3-diol → (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1)

Conditions	Yield
With hypophosphorous acid; sodium nitrite

(5S)-2,2-dimethyl-4c-phenyl-<1,3>dioxan-5r-ylamine → (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1)

Conditions	Yield
With mineral acid

(+-)-2,2-dimethyl-4c-phenyl-<1,3>dioxan-5r-ylamine → (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + (1R,2R)-2-amino-1-phenylpropane-1,3-diol (46032-98-8)

Conditions	Yield
With (1S)-(+)-3-bromocamphor-10-sulfonic acid; ethyl acetate

tert-butyl [(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]carbamate (167082-56-6) → (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h;

formaldehyd (50-00-0) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → C30H39N3O6

Conditions	Yield
In methanol at 20℃; for 16h;	100%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + benzyl chloroformate (501-53-1) → benzyl L-threo-1,3-dihydroxy-1-phenylpropan-2-yl-carbamate (127102-27-6)

Conditions	Yield
With sodium hydrogencarbonate In water Ambient temperature;	99%
With triethylamine In methanol for 1h; Ambient temperature;	91%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + 4-chlorobenzoyl chloride (586-75-4) → (1S,2S)-2-(4'-bromobenzoylamino)-1-phenyl-propane-1,3-diol

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	99%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → C24H23NO4 (1072502-00-1)

Conditions	Yield
In 1,4-dioxane; water at 20℃; for 16h;	99%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → (1S,2S)-1-phenyl-2-amino-1,3-di(trimethylsilanyloxy)-propane (84010-78-6)

Conditions	Yield
With sodium hydrogencarbonate 8 h, 140 degC then allowed to reach room temperature;	98.1%

formaldehyd (50-00-0) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (+)-(1S,2S)-2-(dimethylamino)-1-phenylpropane-1,3-diol (58210-04-1, 67250-22-0, 108147-10-0, 108147-47-3)

Conditions	Yield
With formic acid	98%
With formic acid for 24h; Cooling with ice; Reflux;	88%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + 1,2-bis[di(3',5'-diformylphenyl)phosphanyl]benzene (220096-47-9) → (+)-1,2-bis[bis[3',5'-bis(N-methyliden-(1S,2S)-2-amino-1-phenypropane-1,3-diol)phenyl]phosphanyl]benzene

Conditions	Yield
With trimethyl orthoformate In methanol for 20h; Ambient temperature;	98%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + cyclohexanone (108-94-1) → (2S,3S)-3-hydroxymethyl-2-phenyl-1-oxa-4-azaspiro[4.5]decane

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	98%

ferrocenecarboxylic acid (1271-42-7) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (C5H5)Fe(C5H4CONHCH(CH2OH)(CH(C6H5)(OH)))

Conditions	Yield
With oxalyl dichloride; triethylamine In not given 1) (COCl)2; 2) ligand, (C2H5)3N;	98%

t-butyldimethylsiyl triflate (69739-34-0) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → 2-(tert-butyldimethylsilanyloxy)-1-(t-butyldimethylsilanyloxymethyl)-2-phenylethylamine (191418-28-7)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 23℃; for 16h; Inert atmosphere;	98%

ethyl trifluoroacetate, (383-63-1) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (1S,2S)-1-phenyl-2-trifluoroacetamidopropan-1,3-diol (175690-17-2)

Conditions	Yield
In methanol at 0℃; for 15h;	97%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + 2,4-Dinitrofluorobenzene (70-34-8) → (1S,2S)-2-(2,4-Dinitro-phenylamino)-1-phenyl-propane-1,3-diol (194539-30-5)

Conditions	Yield
	97%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + benzoyl chloride (98-88-4) → (1S,2S)-2-(Benzoylamino)-1-phenyl-1,3-propanediol (72002-77-8)

Conditions	Yield
With potassium hydroxide In diethyl ether	96%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → 2-chloro-4,6-bis{[(2S,3S)-1,3-dihydroxy-3-phenylprop-2-yl]amino}-1,3,5-triazine

Conditions	Yield
With potassium carbonate In tetrahydrofuran at -78 - 20℃;	96%
With potassium carbonate; 18-crown-6 ether In toluene at 0 - 25℃; for 48h;	86%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + 4-methyl-benzoyl chloride (874-60-2) → (1S,2S)-2-(4'-methylbenzoylamino)-1-phenyl-propane-1,3-diol

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	96%

pyridine-2-carbaldehyde (1121-60-4) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (+)-(1S,2S)-1-Phenyl-2-<(2-pyridinylmethylen)amino>-1,3-propandiol

Conditions	Yield
With calcium sulfate In methanol at 50℃; for 1h;	95%

N-benzyloxamic acid ethyl ester (7142-72-5) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → N-benzyl-N'-[(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]oxalamide

Conditions	Yield
In toluene at 20℃; for 2h; Reflux; Inert atmosphere;	95%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + acetyl chloride (75-36-5) → acetate de (S)-2-acetamido-(S)-3-hydroxy-3-phenylpropyle (173094-51-4)

Conditions	Yield
With triethylamine In dichloromethane -5 deg C, 1h; -5 deg C to RT;	94%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + ethyl benzimidate hydrochloride (5333-86-8) → (+)-(4,5-dihydro-2,5-diphenyloxazol-4-yl)methanol (95341-86-9)

Conditions	Yield
With triethylamine In dichloromethane for 15h; Ambient temperature;	94%
In ethanol Condensation;

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + benzoic acid anhydride (93-97-0) → (1S,2S)-2-(Benzoylamino)-1-phenyl-1,3-propanediol (72002-77-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 16h;	94%
With triethylamine In tetrahydrofuran at 20℃;

ortho-diphenylphosphinobenzoic acid (17261-28-8) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (-)-tris-O1,N2,O3-<2-(diphenylphosphino)benzoyl>-L-(+)-threo-2-amino-1-phenyl-1,3-propanediol

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 14h; Ambient temperature;	93.3%

phthalic anhydride (85-44-9) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol (123537-84-8)

Conditions	Yield
In xylene for 2h; Heating;	93%
at 160℃;	88%
at 160℃; under 0.5 Torr;	70%
at 160℃; under 0.5 Torr; for 0.25h;	70%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + 3α,12α-dihydroxy-5β-cholan-24-oic acid 2,5-dioxopyrrolidin-1-yl ester (174069-00-2) → (1S,2S)-1-phenyl-2-deoxycholicacetamidopropane-1,3-diol

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; for 1.5h;	92%

methyl acetimidate (14777-29-8, 85273-25-2) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (4S,5S)-4-Hydroxymethyl-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazole (53732-41-5)

Conditions	Yield
In dichloromethane for 16h; Ambient temperature;	91%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + benzonitrile (100-47-0) → (+)-(4,5-dihydro-2,5-diphenyloxazol-4-yl)methanol (95341-86-9)

Conditions	Yield
potassium carbonate In ethylene glycol; glycerol at 115℃;	91%
In ethylene glycol; glycerol at 110℃; for 20h;	74.7%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + naphthalene-1-carbonic acid chloride (879-18-5) → (1S,2S)-2-(1'-naphthoylamino)-1-phenyl-propane-1,3-diol

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 16h;	91%

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (1S,2S)-2-azido-1-phenyl-1,3-propanediol (952234-39-8)

Conditions	Yield
With potassium carbonate; copper(II) sulfate In methanol at 20℃; for 4h;	91%
With imidazole-1-sulfonyl azide hydrochloride

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + benzaldehyde (100-52-7) → (1S,2S)-(+)-2-(benzylideneamino)-1-phenylpropane-1,3-diol (195144-29-7)

Conditions	Yield
In ethanol for 12h; Heating;	90%
With ethanol
With copper(II) sulfate In methanol for 3h; Heating;

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + p-toluenesulfonyl chloride (98-59-9) → (1S,2S)-N-(4-methylphenylsulphonyl)-2-amino-1-phenyl-1,3-propanediol (130854-92-1)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 24h;	90%
With triethylamine In N,N-dimethyl-formamide for 18h; Ambient temperature;
With triethylamine In N,N-dimethyl-formamide

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) + cholic acid N-succinimidyl ester (70090-26-5) → (1S,2S)-1-phenyl-2-cholicacetamidopropane-1,3-diol

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; for 1.5h;	90%

Upstream product

• 50-00-0 formaldehyd 
• 614-21-1 2-nitroacetophenone 
• 54299-23-9 (+/-)-threo-5-amino-4-phenyl-1,3-dioxane 
• 3306-06-7 2-Amino-1-phenyl-propane-1,3-diol 
• 1377320-83-6 (S)-tert-butyl 4-(hydroxy(phenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 74104-28-2 α-acetamido-β-hydroxypropiophenone 
• 108943-99-3 N-(1-acetoxy-3-oxo-3-phenylpropyl)acetamide 
• 50610-93-0 (1RS,2RS)-2-benzoylamino-1-phenyl-propane-1,3-diol 
• 99857-56-4 (1RS,2SR)-2-bromo-1,3-dimethoxy-1-phenyl-propane 
• 36808-14-7 2-bromo-1-phenylpropane-1,3-diol 
• 69-96-5 dl-threo-phenylserine 
• 75445-32-8 trans-4-(methoxycarbonyl)-5-phenyl-2-oxazoline 
• 2425-28-7 2-Bromo-1-phenylethanol 
• 103-64-0 bromostyrene 

Downstream Products

• 72002-77-8 (1S,2S)-2-(Benzoylamino)-1-phenyl-1,3-propanediol 
• 102312-49-2 (2RS,3SR)-2-amino-3-chloro-3-phenyl-propan-1-ol 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 46032-98-8 (1R,2R)-2-amino-1-phenylpropane-1,3-diol 
• 77250-66-9 ethyl 2-bromobenzimidate 
• 77250-62-5 (4S,5S)-4,5-dihydro-2-(2'-bromophenyl)-4-(hydroxymethyl)-5-phenyloxazole 
• 108303-72-6 3-<(2S,3S)-1,3-dihydroxy-3-phenyl-2-propyl>-4,5-dimethylthiazolium iodide 
• 3306-06-7 2-Amino-1-phenyl-propane-1,3-diol 
• 146985-90-2 (4S,5S)-4-hydroxymethyl-5-phenyloxazolidin-2-one 
• 51594-33-3 (4S,5S)-(-)-2-ethyl-4-hydroxymethyl-5-phenyl-2-oxazoline 
• 41075-43-8 ethyl 2-methylbenzimidate 
• 53732-41-5 (4S,5S)-4-Hydroxymethyl-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazole 
• 160246-26-4 [(4S,5S)-2-(2-Methylsulfanyl-phenyl)-5-phenyl-4,5-dihydro-oxazol-4-yl]-methanol 
• 175477-29-9 (4S,5S)-4-Hydroxymethyl-2-<(4-methylphenyl)sulfanylmethyl>-5-phenyl-4,5-dihydro-1,3-oxazole 

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