CAGED D-ERYTHRO-SPHINGOSINE-1-PHOSPHATE

Base Information

• Chemical Name: CAGED D-ERYTHRO-SPHINGOSINE-1-PHOSPHATE
• CAS No.: 207516-11-8
• Molecular Formula: C26H45N2O7P
• Molecular Weight: 677.775
• Mol file: 207516-11-8.mol

Synonyms:CAGED SPP;CAGED D-ERYTHRO-SPHINGOSINE-1-PHOSPHATE;(2S,3R,4E)-2-AMino-3-hydroxy-4-octadecenyl Phosphoric Acid Bis[1-(2-nitrophenyl)ethyl]ester;Caged SPN-1-P

Chemical Property of CAGED D-ERYTHRO-SPHINGOSINE-1-PHOSPHATE

Chemical Property:

• PSA: 157.64000
• LogP: 7.95840
• Storage Temp.: Hygroscopic, Store under Inert atmosphere -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

Caged D-erythro-sphingosine-1-phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A photolyzable sphingosine 1-phosphate derivative. SPP-mediated intracellular events. Wavelength 254nm. A photolyzable sphingosine 1-phosphate derivative. Caged SPP provides a method to elevate intracellular level of SPP upon ultraviolet irradiation and thus can be utilized as a new tool in studies of SPP-mediated intracellular events. Wavelength 254nm. Caged SPP provides a method to elevate intracellular level of SPP upon ultraviolet irradiation and thus can be utilized as a new tool in studies of SPP-mediated intracellular events. Wavelength 254nm

Technology Process of CAGED D-ERYTHRO-SPHINGOSINE-1-PHOSPHATE

There total 9 articles about CAGED D-ERYTHRO-SPHINGOSINE-1-PHOSPHATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

(4S,5R)-4-{Bis-[1-(2-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester (207516-26-5) → Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester bis-[1-(2-nitro-phenyl)-ethyl] ester (207516-11-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0960-894X(98)00112-7

Reference yield:

1-(2-nitrophenyl)ethan-1-ol (80379-10-8,108530-03-6,142631-59-2,3205-25-2) → Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester bis-[1-(2-nitro-phenyl)-ethyl] ester (207516-11-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / Et₃N / tetrahydrofuran / -78 - 0 °C

2: tetrazole / acetonitrile

3: I₂, pyridine, water / CH₂Cl₂

4: 56 percent / TFA / CH₂Cl₂

With pyridine; 1H-tetrazole; water; iodine; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/S0960-894X(98)00112-7

Reference yield:

N-tert-butyloxycarbonylsphingosine (116467-63-1) → Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester bis-[1-(2-nitro-phenyl)-ethyl] ester (207516-11-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 55 percent / DMAP / CH₂Cl₂

2: p-TsOH / benzene / Heating

3: NaOMe, MeOH

4: tetrazole / acetonitrile

5: I₂, pyridine, water / CH₂Cl₂

6: 56 percent / TFA / CH₂Cl₂

With pyridine; 1H-tetrazole; methanol; dmap; water; iodine; sodium methylate; toluene-4-sulfonic acid; trifluoroacetic acid; In dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0960-894X(98)00112-7

upstream raw materials:

(4S,5R)-4-{Bis-[1-(2-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester

1-(2-nitrophenyl)ethan-1-ol

N-tert-butyloxycarbonylsphingosine

tert-butyl (4S,5R,1'E)-4-(hydroxymethyl)-2,2-dimethyl-5-(pentadec-1'-enyl)-oxazolidine-3-carboxylate

Downstream raw materials:

ortho-nitroso acetophenone

Sphingosine-1-phosphate

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