(2'E,4S,1'R)-4-(1'-hydroxyhexadec-2'-enyl)-1,3-oxazolidin-2-one
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With sodium hydroxide; ethanol at 80℃; for 2.5h; | 100% |
With sodium hydroxide In ethanol at 80℃; for 2.5h; | 100% |
With potassium hydroxide In ethanol for 2.5h; Heating; | 100% |
N-tert-butyloxycarbonylsphingosine
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: N-tert-butyloxycarbonylsphingosine With trifluoroacetic acid In dichloromethane at 50℃; for 2h; Stage #2: With sodium hydroxide; water In dichloromethane pH=~ 10; | 100% |
With hydrogenchloride; water In tetrahydrofuran at 20 - 50℃; for 18h; | 98% |
With trifluoroacetic acid for 0.5h; | 90% |
tert-butyl ((2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-octadec-4-en-2-yl)carbamate
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 1.5h; | 99% |
(4R,5S)-2,2-Di-tert-butyl-4-((E)-pentadec-1-enyl)-[1,3,2]dioxasilinan-5-ylamine
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran at 0℃; for 2h; | 98% |
N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide With sodium hydroxide In ethanol at 20℃; for 2h; Inert atmosphere; Stage #2: With water In ethanol | 96% |
With water; sodium hydroxide In ethanol at 20℃; for 2h; | 82.5% |
With potassium carbonate In ethanol at 50℃; for 5h; | 75% |
2-azido-sphingosine
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With hydrogen sulfide In pyridine; water for 48h; Ambient temperature; | 95% |
With pyridine; hydrogen sulfide In water for 48h; | 95% |
With sodium tetrahydroborate In isopropyl alcohol for 48h; Heating; | 92% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With ammonium hydroxide In methanol at 45℃; for 3h; | 93% |
(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With ammonia; sodium In diethyl ether at -78 - 20℃; for 5h; | 92% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 80℃; for 2h; | 92% |
Conditions | Yield |
---|---|
With ammonia; lithium In tetrahydrofuran for 2h; Heating; | 88% |
(E)-(1S,2R)-2-Benzyloxy-1-benzyloxymethyl-heptadec-3-enylamine
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran at -78℃; for 0.5h; | 88% |
(2S,3R)-(4E)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-octadec-4-en-3-ol
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: (2S,3R)-(4E)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-octadec-4-en-3-ol With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrazine In methanol for 6h; Reflux; Inert atmosphere; | 87% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; water In ethanol at 0℃; for 72h; | 86% |
(2S,3R,4E)-2-Amino-3-benzyloxymethoxy-1-hydroxy-4-octadecene
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With lithium; triethylamine In tetrahydrofuran at -78℃; for 3h; | 85% |
(E)-(2S,3R)-2-Amino-3-benzyloxy-octadec-4-en-1-ol
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran at -78℃; for 0.5h; Birch reduction; | 85% |
2-phenyl-4-(S)-[(1R,2E)-1-(trimethylsilanyl-oxy)hexadec-2-enyl]-1,3-oxazoline
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: 2-phenyl-4-(S)-[(1R,2E)-1-(trimethylsilanyl-oxy)hexadec-2-enyl]-1,3-oxazoline With hydrogenchloride; water In tetrahydrofuran for 18h; Stage #2: With sodium hydroxide; water In methanol for 2h; Heating / reflux; | 85% |
Stage #1: 2-phenyl-4-(S)-[(1R,2E)-1-(trimethylsilanyl-oxy)hexadec-2-enyl]-1,3-oxazoline With hydrogenchloride In tetrahydrofuran at 20℃; for 18h; Stage #2: With sodium hydroxide In methanol for 0.666667h; Heating; | 79% |
threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ2-oxazoline
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ2-oxazoline With hydrogenchloride In tetrahydrofuran; water for 3h; Stage #2: With sodium hydroxide In methanol; water for 1h; Reflux; | 85% |
[(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-heptadec-3-enyl]-carbamic acid tert-butyl ester
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With trifluoroacetic acid for 16h; Ambient temperature; | 83% |
tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate With hydrogenchloride; water In tetrahydrofuran at 75℃; for 12h; Inert atmosphere; Stage #2: With sodium hydroxide In water pH=12; Inert atmosphere; | 82% |
With hydrogenchloride In methanol for 2h; Ambient temperature; | 34% |
With hydrogenchloride |
(2S,3R)-2-amino-1,3-(dibenzyloxy)-octadeca-4-ene
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 80% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: (3aR,5R,6R,6aR)-6-Azido-2,2-dimethyl-5-((E)-pentadec-1-enyl)-tetrahydro-furo[2,3-d][1,3]dioxole With water; trifluoroacetic acid at 25℃; for 2.5h; Stage #2: With sodium periodate In water; acetone at 0 - 30℃; for 2.5h; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 2h; | 79% |
[4S-[4α,5α(E)]]-4-(hydroxymethyl)-5-(1-pentadecenyl)-2-oxazolidinone
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 80℃; for 2h; | 77.5% |
With sodium hydroxide In ethanol at 80℃; for 2.5h; |
(+)-tert-butyl {(1S,2R,3E)-2-Hydroxy-1-[(trityloxy)methyl]heptadec-3-en-1-yl}carbamate
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 3h; | 76% |
(S)-4-((E)-(R)-1-Methoxymethoxy-hexadec-2-enyl)-3-methoxymethyl-oxazolidin-2-one
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 20h; Heating; | 73% |
(2S,3R)-2-amino-1,3-dihydroxyoctadec-4-yne
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In 1,2-dimethoxyethane for 12h; Heating; | 70% |
With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether at 0℃; for 24h; Reduction; | 69% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: (S)-tert-Butyl 4-((R,E)-1-hydroxyhexadec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate With hydrogenchloride; methanol; water for 1.5h; Heating / reflux; Stage #2: With sodium hydroxide In methanol; water | 68% |
C26H50N2O3S
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With borane-ammonia complex; lithium diisopropyl amide In tetrahydrofuran; hexane at 0 - 25℃; Inert atmosphere; | 65% |
Conditions | Yield |
---|---|
With hydrazine hydrate at 90℃; for 20h; | 60% |
(2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With potassium hydroxide; hydrazine hydrate In methanol | 60% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
(2S,3R)-2-amino-1,3-octadecanediol
Conditions | Yield |
---|---|
With hydrogen; 10percent Pd/C In methanol at 24℃; under 760.051 Torr; for 7.5h; Catalytic hydrogenation; | 100% |
With hydrogen; platinum(IV) oxide In methanol for 2.16667h; | 98% |
With 1,4-dioxane; platinum Hydrogenation; | |
With hydrogen; platinum In ethanol | |
With hydrogen |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
acetic anhydride
(2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene
Conditions | Yield |
---|---|
With pyridine | 100% |
With pyridine at 20℃; for 2h; | 99% |
With pyridine at 0 - 20℃; for 18h; | 99% |
ω-azido-hexadecanoic acid
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
ceramide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere; | 99% |
With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; | 85% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
acetic anhydride
N-acetyl-D-erythro-sphingosine
Conditions | Yield |
---|---|
In ethanol for 1h; Ambient temperature; | 97% |
In methanol for 0.5h; Ambient temperature; | 85% |
With methanol |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
di-tert-butyl dicarbonate
N-tert-butyloxycarbonylsphingosine
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water for 0.5h; Ambient temperature; | 97% |
With triethylamine In 1,4-dioxane; water at 20℃; for 0.5h; | 97% |
With triethylamine In 1,4-dioxane; water chemoselective reaction; | 96% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
β-D-galactopyranosyl-(1->4)-α-D-glucopyranosyl fluoride
O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol
Conditions | Yield |
---|---|
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction; | 97% |
With Rhodococcus sp. strain M-777 endoglycoceramidase II glycosynthase mutant E351S/D314Y In 1,2-dimethoxyethane at 37℃; for 72h; pH=5.3; Sonication; Enzymatic reaction; | 95% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In ethyl acetate at 20℃; for 4h; Inert atmosphere; | 97% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
1-nitro-4-trifluoroacetoxy-benzene
N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide
Conditions | Yield |
---|---|
With pyridine for 15h; Ambient temperature; | 96% |
Conditions | Yield |
---|---|
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction; | 96% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
16-bromohexadecanoyl chloride,
D-erythro-2-N-(16'-bromohexadecanoyl)-sphingosine
Conditions | Yield |
---|---|
With sodium acetate In tetrahydrofuran; water at 20℃; for 0.333333h; | 96% |
With sodium acetate In tetrahydrofuran; water at 20℃; for 0.433333h; | 96% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
O-(5-Acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 37℃; for 12h; pH=5.0; Enzymatic reaction; | 95% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
β-D-galactopyranosyl-(1→3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1→4)-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction; | 95% |
6-tetramethylrhodamine-(N-hydroxysuccinimidyl-β-alanine)-amide
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In chloroform; water; N,N-dimethyl-formamide for 15h; | 95% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride
Conditions | Yield |
---|---|
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction; | 94% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
2-azido-sphingosine
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; potassium carbonate In methanol at 20℃; for 12h; | 94% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere; | 94% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux; | 93.4% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux; | 93.2% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
2-azido-sphingosine
Conditions | Yield |
---|---|
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 30℃; for 3h; | 93% |
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; for 3h; | 93% |
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; for 3h; | 93% |
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; | |
With imidazole-1-sulfonyl azide hydrochloride; copper(II) sulphate hydrate In methanol at 20℃; for 12h; |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
15-acetoxypentadecanoic acid
Conditions | Yield |
---|---|
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux; | 93% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
Stage #1: 30-{[(10RS)-16,16,16-d3-10-(methyl-d3)hexadecanoyl]oxy}triacontanoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Stage #2: (2S,3R,4E)-2-amino-4-octadecene-1,3-diol In dichloromethane at 20℃; for 16h; | 93% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
Conditions | Yield |
---|---|
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux; | 92.4% |
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
15-(pentyloxy)pentadecanoic acid
Conditions | Yield |
---|---|
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux; | 92.1% |
IUPAC Name: (E,2S,3R)-2-aminooctadec-4-ene-1,3-diol
Molecular Formula: C18H37NO2
Molecular Weight: 299.49 g/mol
Canonical SMILES: C(=C\CCCCCCCCCCCCC)\[C@H]([C@H](CO)N)O
InChI: InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
Mol File: 123-78-4.mol
EINECS: 204-651-3
Product Categories: Mixed Fatty Acids; Fatty Acid Derivatives & Lipids; Glycerols; Inhibitors; Protein Kinase Inhibitors and Activators; Protein Kinase
Solubility: chloroform: 20 mg/mL, clear, colorless to very faintly yellow
Merck: 13,8821
Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
Nominal Mass: 299
Average Mass: 299.4919
Monoisotopic Mass: 299.282429
H bond acceptors: 3
H bond donors: 4
Freely Rotating Bonds: 18
Polar Surface Area: 21.7
Index of Refraction: 1.489
Molar Refractivity: 92.02 cm3
Molar Volume: 318.7 cm3
Polarizability: 36.47×10-24cm3
Surface Tension: 38.2 dyne/cm
Density: 0.939 g/cm3
Flash Point: 223.5 °C
Enthalpy of Vaporization: 81.24 kJ/mol
Boiling Point: 445.9 °C at 760 mmHg
Melting Point: 81-82 °C
storage temperature: 20 °C
logP(octanol-water): 5.530
Atmospheric OH Rate Constant: 1.34E-10 cm3/molecule-sec at 25 °C
Vapour Pressure of Sphingosine (CAS NO.123-78-4): 7.96E-10 mmHg at 25 °C
1.Sphingosine (CAS NO.123-78-4) does not inhibit protein kinase A or myosin light chain kinase; it inhibits calmodulin-dependent enzymes; it is natural isomer of sphingosine .
2. Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid.
Safety Statements: 22-24/25
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
WGK Germany of Sphingosine (CAS NO.123-78-4): 3
1. Sphingosine (CAS NO.123-78-4), its Synonyms are 2-Aminooctadec-4-ene-1,3-diol ; 4-Octadecene-1,3-diol, 2-amino-, (R-(R*,S*-(E)))- ; (E)-2-Amino-4-octadecan-1,3-diol . It is white crystalline solid.
2. Sphingosine is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholipid.
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