2-Amino-3-hydroxyoctadecyl dihydrogen phosphate

Base Information

• Chemical Name: 2-Amino-3-hydroxyoctadecyl dihydrogen phosphate
• CAS No.: 19794-97-9
• Molecular Formula: C18H40NO5P
• Molecular Weight: 381.493
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID80864905
• Nikkaji Number: J2.162.117J
• Wikidata: Q110184558
• Mol file: 19794-97-9.mol

Synonyms:28508-07-8;(2S,3R)-Dihydrosphingosine 1-phosphate;2-amino-3-hydroxyoctadecyl dihydrogen phosphate;Rel-(2R,3S)-2-amino-3-hydroxyoctadecyl dihydrogen phosphate;(2-amino-3-hydroxyoctadecyl) dihydrogen phosphate;SCHEMBL43371;1,3-Octadecanediol, 2-amino-, 1-(dihydrogen phosphate), (R-(R*,S*))-;DTXSID80864905;AKOS030254882;FT-0667043;Phosphoric acid 2-amino-3-hydroxyoctadecyl ester

Chemical Property of 2-Amino-3-hydroxyoctadecyl dihydrogen phosphate

Chemical Property:

• Vapor Pressure: 2.66E-14mmHg at 25°C
• Boiling Point: 548.2°C at 760 mmHg
• PKA: 1.76±0.10(Predicted)
• Flash Point: 285.3°C
• PSA: 122.82000
• Density: 1.08g/cm³
• LogP: 4.96550
• Storage Temp.: -20°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 18
• Exact Mass: 381.26441037
• Heavy Atom Count: 25
• Complexity: 337

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(C(COP(=O)(O)O)N)O
• Uses: (2-amino-3-hydroxy-octadecoxy)phosphonic acid may be used as a negative control for C2 Ceramide.

Technology Process of 2-Amino-3-hydroxyoctadecyl dihydrogen phosphate

There total 7 articles about 2-Amino-3-hydroxyoctadecyl dihydrogen 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: 79.0%

tert-butyl ((2S,3R)-1-((dimethoxyphosphoryl)oxy)-3-hydroxyoctadecan-2-yl)carbamate (528852-33-7) → sphinganine-1-phosphate (19794-97-9,28508-07-8)

Guidance literature:

With trimethylsilyl bromide; In acetonitrile; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.ejmech.2016.08.008

Reference yield:

(4S)-4r-hydroxymethyl-5c-pentadec-1-en-t-yl-2ξ-phenyl-oxazolidine-3-carboxylic acid benzyl ester (121291-63-2) → sphinganine-1-phosphate (19794-97-9,28508-07-8)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / PtO₂ / ethanol; ethyl acetate

2: H₂ / PtO₂ / acetic acid

3: Py / 5 °C

4: (i) H₂SO₄, aq. EtOH, (ii) H₂, PtO₂, AcOH

With pyridine; hydrogen; platinum(IV) oxide; In ethanol; acetic acid; ethyl acetate;

DOI:10.1021/jo01061a050

Reference yield:

(4S)-4r-hydroxymethyl-5c-pentadecyl-2ξ-phenyl-oxazolidine-3-carboxylic acid benzyl ester (103325-17-3) → sphinganine-1-phosphate (19794-97-9,28508-07-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / PtO₂ / acetic acid

2: Py / 5 °C

3: (i) H₂SO₄, aq. EtOH, (ii) H₂, PtO₂, AcOH

With pyridine; hydrogen; platinum(IV) oxide; In acetic acid;

DOI:10.1021/jo01061a050

upstream raw materials:

((4S)-4r-hydroxymethyl-5c-pentadecyl-2ξ-phenyl-oxazolidin-3-yl)-phosphonic acid diphenyl ester

tert-butyl ((2S,3R)-1-((dimethoxyphosphoryl)oxy)-3-hydroxyoctadecan-2-yl)carbamate

(2S,3R)-2-amino-1,3-octadecanediol

(2S,3R)-2-benzylideneamino-octadecane-1,3-diol

Downstream raw materials:

n-pentadecanal

Refernces

• 1、 Lim, Hyun Suk,Oh, Yong Seok,Suh, Pann Ghill,Chung, Sung Kee. "Syntheses of sphingosine-1-phosphate stereoisomers and analogues and their interaction with EDG receptors.". . p. 237 - 240. Retrieved 2007/10/03.