sphingosine-1-phosphate

Base Information

• Chemical Name: sphingosine-1-phosphate
• CAS No.: 709026-60-8
• Molecular Formula: C₁₆H₃₄NO₅P
• Molecular Weight: 351.423

Synonyms:

Chemical Property of sphingosine-1-phosphate

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

C16Sphingosine-1-phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: C16 Sphingosine-1-phosphate (C16 S1P) is a derivative of sphingosine-1-phosphate (S1P; ) that binds to S1P1/EDG-1, S1P3/EDG-3, and S1P2/EDG-5 receptors with affinities of 115%, 83%, and 103%, respectively, relative to S1P in CHO cells. C16 S1P was increased in postmortem primary open angle glaucoma trabecular meshwork samples.
• Uses: C16-Sphingosine-1-phosphate is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors.

Technology Process of sphingosine-1-phosphate

There total 6 articles about 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:

dimethyl (2S,3R,4E)-2-(tert-butoxycarbonylamino)-3-hydroxyoctadec-4-en-1-ylphosphate (709026-59-5) → sphingosine-1-phosphate (709026-60-8)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmcl.2004.03.001

Reference yield:

Dodecanal (112-54-9) → sphingosine-1-phosphate (709026-60-8)

Guidance literature:

Multi-step reaction with 6 steps

1: DBU; LiCl / tetrahydrofuran / 20 °C

2: aq. HCl / methanol; tetrahydrofuran / 40 °C

3: 75 percent / Zn(BH₄)2 / tetrahydrofuran / -78 °C

4: aq. NaOH / dioxane / 20 °C

5: CBr₄; pyridine / 0 °C

6: TMSBr / CH₂Cl₂ / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; zinc(II) tetrahydroborate; trimethylsilyl bromide; carbon tetrabromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.bmcl.2004.03.001

Reference yield:

<2(S),3(R),4E>-2-amino-4-hexadecene-1,3-diol (6982-09-8) → sphingosine-1-phosphate (709026-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaOH / dioxane / 20 °C

2: CBr₄; pyridine / 0 °C

3: TMSBr / CH₂Cl₂ / 20 °C

With pyridine; sodium hydroxide; trimethylsilyl bromide; carbon tetrabromide; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.bmcl.2004.03.001

upstream raw materials:

dimethyl (2S,3R,4E)-2-(tert-butoxycarbonylamino)-3-hydroxyoctadec-4-en-1-ylphosphate

Dodecanal

<2(S),3(R),4E>-2-amino-4-hexadecene-1,3-diol

tert-butyl ((2S,3R,E)-1,3-dihydroxyhexadec-4-en-2-yl)carbamate

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