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Product FOB Price Min.Order Supply Ability Supplier
SAGECHEM/ D-erythro-Sphingosine /Manufacturer in China/SAGECHEM
Cas No: 123-78-4
No Data No Data Metric Ton/Day SAGECHEM LIMITED Contact Supplier
(2S,3R)-Sphingosine
Cas No: 123-78-4
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
D-erythro-Sphingosine
Cas No: 123-78-4
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
2-aminooctadec-4-ene-1,3-diol
Cas No: 123-78-4
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Pharmaceutical Grade CAS 123-78-4 with competitive price
Cas No: 123-78-4
USD $ 139.0-210.0 / Kilogram 1 Kilogram 1000 Kilogram/Day Zhuozhou Wenxi import and Export Co., Ltd Contact Supplier
BLOOM TECH Advanced API/Technology support D-ERYTHRO-SPHINGOSINE CAS 123-78-4
Cas No: 123-78-4
No Data 1 Gram 3 Metric Ton/Month Shaanxi BLOOM TECH Co.,Ltd Contact Supplier
4-Octadecene-1,3-diol,2-amino-, (2S,3R,4E)-
Cas No: 123-78-4
No Data No Data 10000 Metric Ton/Month Henan Wentao Chemical Product Co., Ltd. Contact Supplier
High Purity (2S,3R)-Sphingosine Cas No: 123-78-4
Cas No: 123-78-4
USD $ 1.0-3.0 / Gram 10 Gram 1000 Kilogram/Month Wuhan Monad Medicine Tech Co.,LTD Contact Supplier
4-Octadecene-1,3-diol,2-amino-, (2S,3R,4E)-
Cas No: 123-78-4
No Data 1 Kilogram 1 Metric Ton/Day Shandong Hanjiang Chemical Co., Ltd. Contact Supplier
China Biggest Factory Manufacturer Supply D-ERYTHRO-SPHINGOSINE CAS 123-78-4
Cas No: 123-78-4
USD $ 1.0-2.0 / Kilogram 1 Kilogram 20 Metric Ton/Month Leader Biochemical Group Contact Supplier

123-78-4 Usage

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.]

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.

Uses

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

Chemical Properties

White Crystalline Solid

Biological Activity

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

123-78-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (S0874)  D-Sphingosine  >96.0%(GC) 123-78-4 25mg 1,490.00CNY Detail
Sigma (S7049)  D-Sphingosine  synthetic 123-78-4 S7049-5MG 1,263.60CNY Detail
Sigma (S7049)  D-Sphingosine  synthetic 123-78-4 S7049-25MG 4,338.36CNY Detail

123-78-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name sphingosine

1.2 Other means of identification

Product number -
Other names [3H]-Sphingosine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123-78-4 SDS

123-78-4Synthetic route

(2'E,4S,1'R)-4-(1'-hydroxyhexadec-2'-enyl)-1,3-oxazolidin-2-one
105308-75-6

(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
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

N-tert-butyloxycarbonylsphingosine

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

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
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(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
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

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
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

2-azido-sphingosine

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

C25H43N3O5

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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-1-benzyloxyoctadec-4-en-3-ol

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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,E)-2-aminooctadec-4-ene-1,3-diol

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With ammonia; lithium In tetrahydrofuran for 2h; Heating;88%
(E)-(1S,2R)-2-Benzyloxy-1-benzyloxymethyl-heptadec-3-enylamine
185681-41-8

(E)-(1S,2R)-2-Benzyloxy-1-benzyloxymethyl-heptadec-3-enylamine

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-octadec-4-en-3-ol

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(2R,3R,E)-ethyl 2-amino-3-hydroxyoctadec-4-enoate hydrochloride

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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-3-benzyloxymethoxy-1-hydroxy-4-octadecene

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(E)-(2S,3R)-2-Amino-3-benzyloxy-octadec-4-en-1-ol

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

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
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ2-oxazoline

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

[(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
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

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
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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)-2-amino-1,3-(dibenzyloxy)-octadeca-4-ene

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

[4S-[4α,5α(E)]]-4-(hydroxymethyl)-5-(1-pentadecenyl)-2-oxazolidinone

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(+)-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
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(S)-4-((E)-(R)-1-Methoxymethoxy-hexadec-2-enyl)-3-methoxymethyl-oxazolidin-2-one

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 20h; Heating;73%
(2S,3R)-2-amino-1,3-dihydroxyoctadec-4-yne
105617-34-3

(2S,3R)-2-amino-1,3-dihydroxyoctadec-4-yne

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

C26H50N2O3S

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With borane-ammonia complex; lithium diisopropyl amide In tetrahydrofuran; hexane at 0 - 25℃; Inert atmosphere;65%
N-acetyl-D-erythro-sphingosine
3102-57-6

N-acetyl-D-erythro-sphingosine

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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-acetamido-1,3-diacetoxyoctadec-4-ene

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate In methanol60%
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

acetic anhydride
108-24-7

acetic anhydride

(2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene
2482-37-3

(2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene

Conditions
ConditionsYield
With pyridine100%
With pyridine at 20℃; for 2h;99%
With pyridine at 0 - 20℃; for 18h;99%
ω-azido-hexadecanoic acid
112668-54-9

ω-azido-hexadecanoic acid

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

ceramide
1298053-54-9

ceramide

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-D-erythro-sphingosine
3102-57-6

N-acetyl-D-erythro-sphingosine

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-tert-butyloxycarbonylsphingosine
116467-63-1

N-tert-butyloxycarbonylsphingosine

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

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

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
109785-20-8

O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

7-(4-(p-tolyldiazenyl)phenyl)heptanoic acid

7-(4-(p-tolyldiazenyl)phenyl)heptanoic acid

N-(7-(4-(p-tolyldiazenyl)phenyl)heptanamide)-(2S,3R)-2-aminooctadec-4-ene-1,3-diol

N-(7-(4-(p-tolyldiazenyl)phenyl)heptanamide)-(2S,3R)-2-aminooctadec-4-ene-1,3-diol

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

1-nitro-4-trifluoroacetoxy-benzene
658-78-6

1-nitro-4-trifluoroacetoxy-benzene

N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide
130967-71-4

N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
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

(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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

globotriaosylsphingosine
126550-86-5

globotriaosylsphingosine

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

16-bromohexadecanoyl chloride,
73782-15-7

16-bromohexadecanoyl chloride,

D-erythro-2-N-(16'-bromohexadecanoyl)-sphingosine
886213-05-4

D-erythro-2-N-(16'-bromohexadecanoyl)-sphingosine

Conditions
ConditionsYield
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

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

(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
94458-63-6

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
ConditionsYield
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 37℃; for 12h; pH=5.0; Enzymatic reaction;95%
C37H61FN2O28

C37H61FN2O28

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

(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
94458-59-0

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
ConditionsYield
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

6-tetramethylrhodamine-(N-hydroxysuccinimidyl-β-alanine)-amide

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

C46H62N4O7

C46H62N4O7

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride
103531-01-7

β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride

(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

(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
ConditionsYield
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

imidazole-1-sulfonyl azide hydrochloride

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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

2-azido-sphingosine
103348-49-8

2-azido-sphingosine

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

α-azidohexadecanoic acid
101442-77-7

α-azidohexadecanoic acid

C34H66N4O3

C34H66N4O3

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

15-(9Z,12Z-octadecadienoyloxy)pentadecanoic acid

15-(9Z,12Z-octadecadienoyloxy)pentadecanoic acid

15-(9Z,12Z-octadeca-9,12-dienoyloxy)pentadecanoic acid (2-hydroxy-1-(hydroxymethyl)heptadec-3-en-yl)amide

15-(9Z,12Z-octadeca-9,12-dienoyloxy)pentadecanoic acid (2-hydroxy-1-(hydroxymethyl)heptadec-3-en-yl)amide

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

15-(octadecyloxy)pentadecanoic acid

15-(octadecyloxy)pentadecanoic acid

15-(octadecyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

15-(octadecyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

2-azido-sphingosine
103348-49-8

2-azido-sphingosine

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

15-acetoxypentadecanoic acid
69186-31-8

15-acetoxypentadecanoic acid

15-(acetoxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

15-(acetoxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions
ConditionsYield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;93%
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

30-{[(10RS)-16,16,16-d3-10-(methyl-d3)hexadecanoyl]oxy}triacontanoic acid

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

N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]-30-{[(10RS)-16,16,16-d3-10-(methyl-d3)hexadecanoyl]oxy}triacontanamid

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

15-(dodecyloxy)pentadecanoic acid

15-(dodecyloxy)pentadecanoic acid

15-(dodecyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

15-(dodecyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions
ConditionsYield
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

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

15-(pentyloxy)pentadecanoic acid
1020733-53-2

15-(pentyloxy)pentadecanoic acid

15-(pentyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

15-(pentyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

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

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d-erythro-Sphingosine (1) and d-erythro-2-azidosphingosine (2) are both prepared from commercially available and cheap d-ribo-phytosphingosine (3) in a yield of 58% and 70%, respectively. A key transformation in the synthesis of d-erythro-sphingosine (1) is the palladium catalyzed regiospecific ...detailed

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Facile and efficient addition of terminal alkynes to benzotriazole esters: synthesis of D-ERYTHRO-SPHINGOSINE (cas 123-78-4) using ynones as the key intermediate09/24/2019

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An efficient building block-based synthetic protocol has been developed for the synthesis of 3-ketosphingoids with various chain lengths using cross metathesis of a Garner’s aldehyde-derived α,β-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus ob...detailed

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