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

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

Uses

1. Used in Biochemical Research:
D-ERYTHRO-SPHINGOSINE is used as a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets. It does not inhibit protein kinase A or myosin light chain kinase but inhibits calmodulin-dependent enzymes.
2. Used in Apoptosis Induction:
D-ERYTHRO-SPHINGOSINE is used to inhibit protein kinase C and calmodulin-dependent enzymes, which in turn induces apoptosis, a process of programmed cell death.
3. Used in Cell Membrane Constituents:
D-ERYTHRO-SPHINGOSINE is a constituent of cell membranes, playing a crucial role in their structure and function.
4. Used in Pharmaceutical Applications:
D-ERYTHRO-SPHINGOSINE has been used in various pharmaceutical applications, such as a standard in liquid chromatography tandem mass spectrometry for the quantification of epidermal ceramides.
5. Used in Respiratory Epithelial Cell Studies:
D-ERYTHRO-SPHINGOSINE has been utilized in sphingosine inhalation studies in mice to evaluate its therapeutic potential in respiratory epithelial cells.
6. Used in Pseudomonas aeruginosa Strain Research:
D-ERYTHRO-SPHINGOSINE has been employed to investigate its effect on Pseudomonas aeruginosa strains, which are a group of bacteria commonly found in the environment and can cause infections in humans.
7. Used in the Production of Cerebrosides:
D-ERYTHRO-SPHINGOSINE is a component in the production of cerebrosides, a class of glycolipids in which a single sugar unit is bound to a sphingolipid. The most common cerebrosides are galactocerebrosides, containing the sugar group galactose. They are found in the plasma membranes of neural tissue and are abundant in the myelin sheaths of neurons.

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

• 123-78-4 erythro-(E)-2-amino-4-octadecene-1,3-diol 
• 105617-34-3 (2S,3R)-2-amino-1,3-dihydroxyoctadec-4-yne 
• 3542-12-9 (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol 
• 103348-49-8 2-azido-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 
• 124-25-4 myristylaldehyde 
• 15890-72-9 laurylmagnesium bromide 
• 473-81-4 glyceric acid 
• 1438399-43-9 C₂₆H₅₀N₂O₃S 
• 67-56-1 methanol 
• 2733-33-7 (+/-)-threo-2-amino-octadec-4-yne-1,3-diol 
• 2733-33-7 (+/-)-erythro-2-amino-octadec-4-yne-1,3-diol 
• 81819-45-6 (Z)-(2S,3S)-2-Amino-3-hydroxy-octadec-4-enoic acid 

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 
• 16170-10-8 N-myristoylceramide 
• 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 
• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 3542-12-9 (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol 
• 992-35-8 (2S,3R,4E)-2-benzamido-1,3-dibenzoyloxyoctadec-4-ene 
• 2482-37-3 dl-threo-triacetylsphingosine 

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