123-78-4

Basic information

• Product Name: D-ERYTHRO-SPHINGOSINE
• Synonyms: SPHINGOSINE;SPHINGOSINE, C18 CHAIN;SPHINGOSINE, D-ERYTHRO;TRANS D-THREO-SPHINGOSINE;TRANS D-ERYTHRO-SPHINGOSINE;TRANS-D-ERYTHRO-2-AMINO-4-OCTADECENE-1,3-DIOL;BRAIN SPHINGOSINE;BRAIN, BOVINE
• CAS NO: 123-78-4
• Molecular Formula: C₁₈H₃₇NO₂
• Molecular Weight: 299.49
• EINECS: 204-651-3
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators;Protein Kinase;Amines
• Mol File: 123-78-4.mol
• Article Data: 102

Chemical Properties

• Melting Point: 81-82 °C
• Boiling Point: 440.8°C (rough estimate)
• Flash Point: 223.486 °C
• Appearance: White to cream/Powder or Waxy Solid
• Density: 0.9758 (rough estimate)
• Vapor Pressure: 7.96E-10mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: −20°C
• Solubility: chloroform: 20 mg/mL, clear, colorless to very faintly yell
• PKA: 11.80±0.45(Predicted)
• Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
• Merck: 14,8747
• BRN: 1727294
• CAS DataBase Reference: D-ERYTHRO-SPHINGOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: D-ERYTHRO-SPHINGOSINE(123-78-4)
• EPA Substance Registry System: D-ERYTHRO-SPHINGOSINE(123-78-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 1-8-10
• Hazardous Substances Data: 123-78-4(Hazardous Substances Data)

Usage

Description

Sphingosine (123-78-4) is an inhibitor of protein kinase C (IC50 = 1-3 μM).1 It is abundant in cell membranes and is an important mediator in various biochemical pathways.2-4

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 123-78-4 differently. You can refer to the following data:
1. Selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine
2. D-erythro-Sphingosine is used to inhibits protein kinase C and calmodulin-dependent enzymes, induces apoptosis. And also used to constituent of cell membranes.
3. Sphingosine (d18:1) has been used:for sphingosine inhalations studies in mice to evaluate its therapeutic potential in respiratory epithelial cellsto investigate its effect on Pseudomonas aeruginosa strainsas a standard in liquid chromatography tandem mass spectrophotometry for the quantification of epidermal ceramides

Definition

cerebroside: Any one of a class ofglycolipids in which a single sugarunit is bound to a sphingolipid. The most commoncerebrosides are galactocerebrosides,containing the sugar group galactose;they are found in the plasma membranesof neural tissue and are abundantin the myelin sheaths ofneurones.

General Description

Sphingosine (d18:1) is a spingoid base present in plant and animals. It has 2-amino-1,3-diol functionality and its extraction from animal tissue is laborious. Sphingosine (d18:1) synthesis is performed by chirospecific method using D-galactose.

Biological Activity

Inhibitor of protein kinase C and calmodulin-dependent enzymes, but may stimulate mast cells by activation of protein kinase C.

Biochem/physiol Actions

A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase?A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.

Purification Methods

D-Sphingosine is purified by recrystallisation from EtOAc, Et2O or pet ether (60-80o). It is insoluble in H2O but is soluble in Me2CO, EtOH and MeOH. It has IR bands at 1590 and 875 cm-1, and is characterised as the tribenzoate m 122-123o (from 95% EtOH). [Tipton Biochemical Preparations 9 127 1962.]

References

1) Merrill et al., (1989) Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds; Biochemistry, 28 3138 2) Ohanian and Ohanian (2001) Sphingolipids in mammalian cell signaling; Cell. Mol. Life Science, 58 2053 3) Ruvolo (2003) Intracellular signal transduction pathways activated by ceramide and its metabolites; Pharm. Res., 47 383 4) Olivier (2002) Sphingosine in apoptosis signaling; Biochim. Biophys. Acta, 1585 153

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+

Synthetic route

(2'E,4S,1'R)-4-(1'-hydroxyhexadec-2'-enyl)-1,3-oxazolidin-2-one (105308-75-6) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (116467-63-1) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (221455-36-3) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (498541-46-1) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (130967-71-4) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (103348-49-8) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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%

C25H43N3O5 → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With ammonium hydroxide In methanol at 45℃; for 3h;	93%

(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol (511542-07-7) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With ammonia; sodium In diethyl ether at -78 - 20℃; for 5h;	92%

(4S,5R)-4-(hydroxymethyl)-5-(pentadec-1-en-1-yl)oxazolidin-2-one → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With sodium hydroxide In ethanol; water at 80℃; for 2h;	92%

(2S,3R,E)-2-aminooctadec-4-ene-1,3-diol (3542-12-9) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With ammonia; lithium In tetrahydrofuran for 2h; Heating;	88%

(E)-(1S,2R)-2-Benzyloxy-1-benzyloxymethyl-heptadec-3-enylamine (185681-41-8) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (1094213-80-5) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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%

(2R,3R,E)-ethyl 2-amino-3-hydroxyoctadec-4-enoate hydrochloride → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With sodium tetrahydroborate; water In ethanol at 0℃; for 72h;	86%

(2S,3R,4E)-2-Amino-3-benzyloxymethoxy-1-hydroxy-4-octadecene (133859-61-7) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With lithium; triethylamine In tetrahydrofuran at -78℃; for 3h;	85%

(E)-(2S,3R)-2-Amino-3-benzyloxy-octadec-4-en-1-ol (850223-35-7) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (572922-39-5) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (78739-31-8) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (198009-73-3) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (115464-03-4) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (148289-52-5) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With ammonia; sodium In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	80%

(3aR,5R,6R,6aR)-6-Azido-2,2-dimethyl-5-((E)-pentadec-1-enyl)-tetrahydro-furo[2,3-d][1,3]dioxole → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (128751-66-6) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (299172-62-6) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (178550-59-9) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With sodium hydroxide In ethanol for 20h; Heating;	73%

(2S,3R)-2-amino-1,3-dihydroxyoctadec-4-yne (105617-34-3) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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%

(S)-tert-Butyl 4-((R,E)-1-hydroxyhexadec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

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 (1438399-43-9) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With borane-ammonia complex; lithium diisopropyl amide In tetrahydrofuran; hexane at 0 - 25℃; Inert atmosphere;	65%

N-acetyl-D-erythro-sphingosine (3102-57-6) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With hydrazine hydrate at 90℃; for 20h;	60%

(2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene (2482-37-3) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In methanol	60%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → (2S,3R)-2-amino-1,3-octadecanediol (764-22-7, 2304-75-8, 3102-56-5, 3102-60-1, 6036-76-6, 6036-86-8, 13552-09-5, 15639-50-6, 73938-69-9)

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 (123-78-4) + acetic anhydride (108-24-7) → (2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene (2482-37-3)

Conditions	Yield
With pyridine	100%
With pyridine at 20℃; for 2h;	99%
With pyridine at 0 - 20℃; for 18h;	99%

ω-azido-hexadecanoic acid (112668-54-9) + (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → ceramide (1298053-54-9)

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 (123-78-4) + acetic anhydride (108-24-7) → N-acetyl-D-erythro-sphingosine (3102-57-6)

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 (123-78-4) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyloxycarbonylsphingosine (116467-63-1)

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 (123-78-4) + β-D-galactopyranosyl-(1->4)-α-D-glucopyranosyl fluoride (7584-85-2, 7792-96-3, 30048-41-0, 66701-54-0, 71328-30-8, 103531-01-7, 149342-82-5) → O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol (109785-20-8)

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 (123-78-4) + 7-(4-(p-tolyldiazenyl)phenyl)heptanoic acid → N-(7-(4-(p-tolyldiazenyl)phenyl)heptanamide)-(2S,3R)-2-aminooctadec-4-ene-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 (123-78-4) + 1-nitro-4-trifluoroacetoxy-benzene (658-78-6) → N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide (130967-71-4)

Conditions	Yield
With pyridine for 15h; Ambient temperature;	96%

(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-6-((2R,3S,4R,5R,6R)-6-Fluoro-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol + (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → globotriaosylsphingosine (126550-86-5)

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 (123-78-4) + 16-bromohexadecanoyl chloride, (73782-15-7) → D-erythro-2-N-(16'-bromohexadecanoyl)-sphingosine (886213-05-4)

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%

5-acetylamino-2-[2-(6-fluoro-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-4-hydroxy-6-(1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid + (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → 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 (94458-63-6)

Conditions	Yield
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 37℃; for 12h; pH=5.0; Enzymatic reaction;	95%

C37H61FN2O28 + (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → 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 (94458-59-0)

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 (933058-16-3) + (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → C46H62N4O7

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 (123-78-4) + β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride (103531-01-7) → (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-((E)-(2S,3R)-2-Amino-3-hydroxy-octadec-4-enyloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Conditions	Yield
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction;	94%

imidazole-1-sulfonyl azide hydrochloride + (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → 2-azido-sphingosine (103348-49-8)

Conditions	Yield
With copper(ll) sulfate pentahydrate; potassium carbonate In methanol at 20℃; for 12h;	94%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + α-azidohexadecanoic acid (101442-77-7) → C34H66N4O3

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 (123-78-4) + 15-(9Z,12Z-octadecadienoyloxy)pentadecanoic acid → 15-(9Z,12Z-octadeca-9,12-dienoyloxy)pentadecanoic acid (2-hydroxy-1-(hydroxymethyl)heptadec-3-en-yl)amide

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	93.4%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + 15-(octadecyloxy)pentadecanoic acid → 15-(octadecyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	93.2%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → 2-azido-sphingosine (103348-49-8)

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 (123-78-4) + 15-acetoxypentadecanoic acid (69186-31-8) → 15-(acetoxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	93%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + 30-{[(10RS)-16,16,16-d3-10-(methyl-d3)hexadecanoyl]oxy}triacontanoic acid → N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]-30-{[(10RS)-16,16,16-d3-10-(methyl-d3)hexadecanoyl]oxy}triacontanamid

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 (123-78-4) + 15-(dodecyloxy)pentadecanoic acid → 15-(dodecyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	92.4%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + 15-(pentyloxy)pentadecanoic acid (1020733-53-2) → 15-(pentyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

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

Upstream product

• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 128751-66-6 [4S-[4α,5α(E)]]-4-(hydroxymethyl)-5-(1-pentadecenyl)-2-oxazolidinone 
• 130967-71-4 N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide 
• 198009-73-3 [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-heptadec-3-enyl]-carbamic acid tert-butyl ester 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 115464-01-2 (4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester 
• 850223-35-7 (E)-(2S,3R)-2-Amino-3-benzyloxy-octadec-4-en-1-ol 
• 130259-14-2 (2S,3R,4E)-2-azido-3-O-benzylsphingosine 
• 498582-80-2 tert-butyl (2S,4R,5S)-4-((E)-pentadec-1-enyl)-2-phenyl-4-vinyl-1,3-dioxan-5-ylcarbamate 
• 947325-52-2 tert-butyl (S,E)-(1-((tert-butyldimethylsilyl)oxy)-3-oxooctadec-4-en-2-yl)carbamate 
• 221455-36-3 tert-butyl ((2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-octadec-4-en-2-yl)carbamate 
• 2733-33-7 (+/-)-threo-2-amino-octadec-4-yne-1,3-diol 
• 18696-97-4 1,1-diethoxy-hexadec-2-yne 
• 2733-33-7 (+/-)-erythro-2-amino-octadec-4-yne-1,3-diol 

Downstream Products

• 74713-60-3 N-lauroylceramide 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 105563-12-0 N-CBZ-dihydrosphingosine 
• 638-53-9 tridecanoic acid 
• 544-63-8 n-tetradecanoic acid 
• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 2482-37-3 dl-threo-triacetylsphingosine 
• 2482-37-3 dl-erythro-triacetylsphingosine 
• 74713-59-0 N-octanoylsphingosine 
• 54336-64-0 (2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol 
• 27888-44-4 (2S,3R)-N-(docosanoate)-1,3-dihydroxy-2-amino-octadeca-4-(E)-ene 
• 7344-02-7 N-arachidoyl-D-erythro-sphingosine 
• 17673-74-4 N-tetracosanoyl-D-erythro-sphingosine 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 

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Relevant articles and documents

An efficient synthesis of D-erythro- and D-threo-sphingosine from D-glucose: Olefin cross-metathesis approach

(Chemical Equation Presented) The D-erythro- and D-threo-sphingosine were synthesized via E-selective olefin cross-metathesis using a D-glucose-derived building block and long-chain terminal alkene.

Highly Diastereoselective Synthesis of D-threo- and D-erythro-Sphingosine from Glycidol

D-Threo- and D-erythro-sphingosine, (1) and (2), inhibitors of protein kinase C, have been efficiently synthesized from glycidol through (R)-4-methoxycarbonyloxazolidinone (3) by selective mono-alkylation followed by highly diastereoselective reduction of the tin-substituted pentadecenyl ketone 5.

Amplification of a FRET Probe by Lipid–Water Partition for the Detection of Acid Sphingomyelinase in Live Cells

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Liposomal FRET Assay Identifies Potent Drug-Like Inhibitors of the Ceramide Transport Protein (CERT)

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