(2S,3S,4R)-2-Amino-1,3,4-octadecanetriol supplier

Name
PHYTOSPHINGOSINE
EINECS
CAS No. 554-62-1
Article Data59
CAS DataBase
Density 0.983 g/cm³
Solubility 2.6mg/L at 20℃
Melting Point 102 °C
Formula C₁₈H₃₉NO₃
Boiling Point 483.733 °C at 760 mmHg
Molecular Weight 317.513
Flash Point 246.353 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,3,4-Octadecanetriol,2-amino-, D-ribo- (8CI);1,3,4-Octadecanetriol, 2-amino-, [2S-(2R*,3R*,4S*)]-;Phytosphingosine (6CI);(+)-D-ribo-Phytosphingosine;4-D-Hydroxysphinganine;4D-Hydroxysphinganine;C18-Phytosphingosine;Sphinganine, 4-D-hydroxy-;D-ribo-1,3,4-Trihydroxy-2-aminooctadecane;(2S,3S,4R)-2-Aminooctadecane-1,3,4-triol;
PSA 86.71000
LogP 3.81930

Synthetic route

: 471891-18-6
(2S,3S,4R,5Z)-2-azido-3,4-dibenzyloxy-5-octadecen-1-ol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal	96%

: 124127-36-2
(S)-tert-butyl 4-[(1S,2R)-1,2-dihydroxyhexadecyl]-2,2-dimethyloxazolidine-3-carboxylate

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With water; trifluoroacetic acid for 0.25h;	95%
With trifluoroacetic acid In water at 20℃; for 0.5h; Hydrolysis;	92%
With trifluoroacetic acid In water	68%
With trifluoroacetic acid In water for 1h; Hydrolysis;
With trifluoroacetic acid at 20℃; for 0.333333h;

: 117168-59-9
(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran 1.) 30 min, RT; 2.) 1 h, reflux;	95%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 48h;	94%
With pyridine; hydrogen sulfide; water Ambient temperature;	87%

: (2S,3S,4R)-2-azidooctadec-6-yne-1,3,4-triol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol Ambient temperature;	93%

: 925222-46-4
(2S,3S,4R)-2-[(R)-1-phenylethylamino]octadecane-1,3,4-triol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In ethanol at 20℃; under 5171.48 Torr;	92%

: 1094213-81-6
(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-3-hydroxy-octadecan-4-yl benzoate

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
Stage #1: (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-3-hydroxy-octadecan-4-yl benzoate With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrazine In methanol for 7h; Reflux; Inert atmosphere;	89%

: 111394-76-4, 111466-47-8
(2S,3S,4R)-2-amino-1-benzoyloxy-octadecane-3,4-diol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With potassium hydroxide In methanol 22 deg C, 12 h. then 60 deg C, 3 h.;	85%

: 175696-50-1
tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With trifluoroacetic acid In water at 20℃; for 0.5h;	82%
With trifluoroacetic acid In water at 20℃; for 0.5h; Inert atmosphere;	82%
With trifluoroacetic acid at 20℃; for 0.5h;	43%

: (2R,3S,4R)-2-amino-3-hydroxyoctadecane-1,4-lactone hydrochloride

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 72h; Heating;	82%

: 219697-93-5
(2S,3S,4R)-2-benzylamino-1,3,4-dihydroxyoctadecane

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In ethanol under 2585.74 Torr; for 16h;	80%
With hydrogen; palladium dihydroxide In methanol Yield given;

: (2S,3S,4R)-(2,3-bis-benzyloxy-1-hydroxymethyl-heptadecyl)-carbamic acid benzyl ester

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With 20% palladium hydroxide-activated charcoal; hydrogen In methanol at 20℃; under 2585.81 Torr; for 48h;	80%

: 309946-71-2
(3R,4S,5R)-3-Azido-4-hydroxy-5-tetradecyl-dihydro-furan-2-one

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 63 - 65℃; for 2h; Reduction;	78%

: 947747-31-1
C44H53N3O3

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	66%

: 600168-67-0
2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
Stage #1: 2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol In methanol; acetic acid at 60℃; Stage #2: With triphenylphosphine In pyridine; water Staudinger reaction;	65%

: 1233506-76-7
(2S,3S,4R)-2-azidooctadec-5-yne-1,3,4-triol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With Pearlman's catalist; hydrogen In methanol	63%

: 174272-23-2
(2S,3S,4R)-2-(p-tolylsulfonamido)-1,3,4-octadecanetriol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With sodium tetrahydroborate; 1,5-dimethoxynaphthalene In ethanol; water for 10h; Ambient temperature; Irradiation;	62.6%

: 1643949-12-5
C32H64N4O4SSi

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
Stage #1: C32H64N4O4SSi With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 65℃; Inert atmosphere; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0℃; Inert atmosphere;	57%

: (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-2,2-dimethyl-5-((Z)-tetradec-1-enyl)-[1,3]dioxolane

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol; chloroform; water	52%

: 13265-71-9
(2S,3S,4R)-2-(phthalimido)-octadecane-1,3,4-triol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol

: 409085-68-3
(+)-2-Cyclohexanoylamino-1,3,4-trihydroxy-octadecan

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With methanol; sulfuric acid

: 70287-09-1
(2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal

: 127924-67-8
(2S,3S,4R)-2-Hydrazino-octadecane-1,3,4-triol; hydrochloride

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; platinum(IV) oxide In ethanol; water for 24h;

: 157117-30-1
N-[(1S,2S,3R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2,3-dihydroxy-heptadecyl]-benzamide

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 95℃; for 12h; Yield given;

: 181824-87-3
[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid tert-butyl ester

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With potassium hydroxide; trifluoroacetic acid 2.) MeOH; Yield given. Multistep reaction;

: 157117-26-5
(1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide 1.) THF, water, room temperature, 5 h, 2.) THF, water, ethanol, 95 deg C, 12 h; Yield given; Multistep reaction;
Multi-step reaction with 3 steps 1: 4N HCl / tetrahydrofuran / 24 h / Ambient temperature 2: aq. NaOH / Ambient temperature 3: NaOH / aq. ethanol / 12 h / 95 °C View Scheme

: 603132-05-4
(4S,5S)-5-Azido-4-((R)-1-benzyloxy-pentadecyl)-2-(4-methoxy-phenyl)-[1,3]dioxane

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol

: 67-56-1
methanol

: (2S,3S,4R,2'R)-2-(2'-hydroxy-9'Z-ene-tetracosanoylamino)-octadecane-1,3,4-triol

A: 554-62-1
D-ribo-phytosphingosine

B: methyl 2-hydroxy-9Z-ene-tetracosanate

Conditions

Conditions	Yield
With hydrogenchloride at 60℃; for 6h;

...Expand

: 67-56-1
methanol

: 2,3-dihydroxy-N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]tetracosanamide

A: 554-62-1
D-ribo-phytosphingosine

B: methyl 2,3-dihydroxytetracosanoate

Conditions

Conditions	Yield
In water at 80℃; for 16h;

...Expand

: 202812-10-0
(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1,3,4-octadecanetriol

: 554-62-1
D-ribo-phytosphingosine

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In methanol

: 554-62-1
D-ribo-phytosphingosine

: 383-63-1
ethyl trifluoroacetate,

: 354149-81-8
2,2,2-trifluoro-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide

Conditions

Conditions	Yield
In ethanol at 20℃; for 20h;	100%
In ethanol at 20℃; for 12h; Inert atmosphere;	92%
In ethanol at 25℃;	90%

: 554-62-1
D-ribo-phytosphingosine

: 117168-59-9
(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

Conditions

Conditions	Yield
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; for 18h;	100%
With copper(ll) sulfate pentahydrate; triflic azide; potassium carbonate In methanol; water at 20℃; Inert atmosphere;	100%
With triflic azide; copper(II) sulfate In methanol; dichloromethane; water for 18h;	98%

: 554-62-1
D-ribo-phytosphingosine

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1224436-75-2
(2S,3S,4R)-2-amino-1-((tert-butyldiphenylsilyl)oxy)octadecane-3,4-diol

Conditions

Conditions	Yield
With pyridine regioselective reaction;	100%
With pyridine

: 554-62-1
D-ribo-phytosphingosine

: 117-08-8
tetrachlorophthalic anhydride

: 1535186-19-6
(2S,3S,4R)-2-(tetrachlorophthalimido)-octadecan-1,3,4-triol

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 0.166667h; Inert atmosphere;	100%
In N,N-dimethyl-formamide at 150℃; for 0.0833333h; Inert atmosphere;

: 554-62-1
D-ribo-phytosphingosine

: 506-46-7
1-hexacosanoic acid

: 182362-51-2
hexacosanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl) amide

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 168h;	100%

: 554-62-1
D-ribo-phytosphingosine

: 98-88-4
benzoyl chloride

: 1987-40-2
(2S,3R,4R)-2-(N-benzoyl)amino-octadecane-1,3,4-triol

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;	99%
With triethylamine In tetrahydrofuran for 0.5h;	99%
With sodium hydroxide; diethyl ether

: 554-62-1
D-ribo-phytosphingosine

: 108-24-7
acetic anhydride

: 13018-48-9
N,O,O,O-tetraacetyl-D-ribo-phytosphingosine

Conditions

Conditions	Yield
With pyridine; dmap for 18h; Ambient temperature;	98%
With pyridine at 20℃;	98%
With pyridine; dmap at 20℃; Acetylation;	94%

: 554-62-1
D-ribo-phytosphingosine

: 24424-99-5
di-tert-butyl dicarbonate

: 175696-50-1
tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	98%
With sodium hydroxide In ethanol; water at 0 - 20℃; Inert atmosphere;	96%
With potassium carbonate In methanol for 1h;	95%

: 554-62-1
D-ribo-phytosphingosine

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: 1549685-07-5
(2S, 3S, 4R)-2-[N-(9-fluorenylmethyloxycarbonyl)amino]octadecane-1,3,4-triol

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere;	97%

: 554-62-1
D-ribo-phytosphingosine

: 57-11-4
stearic acid

: 34354-88-6
(2S,3S,4R)-2-(N-stearoylamino)octadecane-1,3,4-triol

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane	96%
With potassium fluoride; sodium persulfate; 1,4-dimethyl-4H-1,2,4-triazol-1-ium chloride In tert-butyl methyl ether at 20℃; for 36h;	84%
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 40h;	68%

: 554-62-1
D-ribo-phytosphingosine

: 3855-45-6
triflic azide

: 117168-59-9
(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

Conditions

Conditions	Yield
	96%

: 22102-68-7
hexacosanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

: 554-62-1
D-ribo-phytosphingosine

: 182362-51-2
hexacosanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl) amide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 50℃; for 14h;	95%
In tetrahydrofuran	94%
With triethylamine In tetrahydrofuran at 50℃; for 20h; Inert atmosphere;	88%

: 554-62-1
D-ribo-phytosphingosine

: 5333-86-8
ethyl benzimidate hydrochloride

: 572922-35-1
2-phenyl-4-(S)-[(1R,2R)-1,2-dihydroxyhexadecyl]-1,3-oxazoline

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 40℃; for 48h;	95%
With triethylamine In dichloromethane at 40℃; for 48h;	95%

: 554-62-1
D-ribo-phytosphingosine

: 20392-34-1
3-(isocyanatomethyl)heptane

: C27H56N2O4

Conditions

Conditions	Yield
In tetrahydrofuran	95%

: 554-62-1
D-ribo-phytosphingosine

: 103-71-9
phenyl isocyanate

: C25H44N2O4

Conditions

Conditions	Yield
In tetrahydrofuran	95%

: 554-62-1
D-ribo-phytosphingosine

: C40H70N6O8

: kozupeptin A

Conditions

Conditions	Yield
In chloroform at 20℃; for 6h;	95%
In chloroform at 20℃; for 2.5h;	51%

: 554-62-1
D-ribo-phytosphingosine

: 929-77-1
behenic acid methyl ester

: 164576-03-8
(2S,3S,4R)-2-docosanoylamino-1,3,4-octadecanetriol

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 55℃;	94.1%

: 554-62-1
D-ribo-phytosphingosine

: 407-25-0
trifluoroacetic anhydride

: 354149-81-8
2,2,2-trifluoro-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; for 18h;	94%
With potassium carbonate In dichloromethane at 20℃; for 18h;	94%
With potassium carbonate In dichloromethane at 20℃; for 18h;	94%

: 554-62-1
D-ribo-phytosphingosine

: 15-(nonyloxy)pentadecanoic acid

: 15-(nonyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	93.1%

: 554-62-1
D-ribo-phytosphingosine

: 15-(undecyloxy)pentadecanoic acid

: 15-(undecyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	92.8%

: 554-62-1
D-ribo-phytosphingosine

: 15-(octadecanoyloxy)pentadecanoic acid

: 15-(octadecanoyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	92.1%

: 554-62-1
D-ribo-phytosphingosine

: 501-53-1
benzyl chloroformate

: 634587-38-5
(2S,3R,4R)-2-benzyloxycarbonylamino-1,3,4-octadecanetriol

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 20℃;	92%
With sodium hydrogencarbonate In 1,4-dioxane at 20℃;	90%
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃;	90%
With sodium hydrogencarbonate In 1,4-dioxane; ethyl acetate at 20℃;	90%
With sodium carbonate In water; acetone at 20℃;

: 554-62-1
D-ribo-phytosphingosine

: 506-46-7
1-hexacosanoic acid

: 871541-12-7
C48H97NO4

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 6h;	92%

: 554-62-1
D-ribo-phytosphingosine

: 111-36-4
n-butyl isocyanide

: C23H48N2O4

Conditions

Conditions	Yield
In tetrahydrofuran	92%

: 554-62-1
D-ribo-phytosphingosine

: 69186-31-8
15-acetoxypentadecanoic acid

: 15-(acetoxy)pentadecanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	92%

(2S,3S,4R)-2-Amino-1,3,4-octadecanetriol Specification

The 1,3,4-Octadecanetriol,2-amino-, (2S,3S,4R)-, with the CAS registry number 554-62-1, is also known as 4-D-Hydroxysphinganine. This chemical's molecular formula is C₁₈H₃₉NO₃ and molecular weight is 317.51. What's more, its systematic name is (2S,3S,4R)-2-Aminooctadecane-1,3,4-triol. Its storage temperature is -20 °C.

Physical properties of 1,3,4-Octadecanetriol,2-amino-, (2S,3S,4R)- are: (1)ACD/LogP: 4.52; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.468; (4)ACD/LogD (pH 7.4): 2.431; (5)ACD/BCF (pH 5.5): 1.423; (6)ACD/BCF (pH 7.4): 13.06; (7)ACD/KOC (pH 5.5): 6.079; (8)ACD/KOC (pH 7.4): 55.808; (9)#H bond acceptors: 4; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 20; (12)Polar Surface Area: 86.71 Å²; (13)Index of Refraction: 1.49; (14)Molar Refractivity: 93.456 cm³; (15)Molar Volume: 322.982 cm³; (16)Polarizability: 37.049×10^-24cm³; (17)Surface Tension: 41.477 dyne/cm; (18)Density: 0.983 g/cm³; (19)Flash Point: 246.353 °C; (20)Enthalpy of Vaporization: 86.297 kJ/mol; (21)Boiling Point: 483.733 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O
(2)InChI: InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1
(3)InChIKey: AERBNCYCJBRYDG-KSZLIROESA-N

Product Name

PHYTOSPHINGOSINE

Synthetic route

(2S,3S,4R)-2-Amino-1,3,4-octadecanetriol Specification

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