2-Azido-4-octadecen-1,3-diol

Base Information

• Chemical Name: 2-Azido-4-octadecen-1,3-diol
• CAS No.: 103348-49-8
• Molecular Formula: C18H35N3O2
• Molecular Weight: 325.495
• Hs Code.: 2929909090
• Nikkaji Number: J962.180F
• Mol file: 103348-49-8.mol

Synonyms:2-azido-4-octadecen-1,3-diol;2-azidosphingosine

Chemical Property of 2-Azido-4-octadecen-1,3-diol

Chemical Property:

• Appearance/Colour: White to Off-White Solid
• Melting Point: 53-54 ºC
• PSA: 90.21000
• LogP: 4.72856
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 16
• Exact Mass: 325.27292737
• Heavy Atom Count: 23
• Complexity: 328

Purity/Quality:

98%Min ^*data from raw suppliers

Azido-erythro-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(CO)N=[N+]=[N-])O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N=[N+]=[N-])O
• Uses: A derivative of Sphingosine, a 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 kina se; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine.

Technology Process of 2-Azido-4-octadecen-1,3-diol

There total 71 articles about 2-Azido-4-octadecen-1,3-diol 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: 99.0%

(2S,3S,4E)-2-azidooctadec-1,3-O-di-(tert-butyl)silanediyl-4-ene-1,3-diol (498541-45-0) → 2-azido-sphingosine (103348-49-8)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(02)01807-5

Reference yield: 99.0%

(2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol (916159-70-1) → 2-azido-sphingosine (103348-49-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo0614543

Reference yield: 98.0%

(2R,3R,4E)-2-Azido-1,3-di-O-benzoyloctadec-4-ene-1,3-diol (202464-99-1) → 2-azido-sphingosine (103348-49-8)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

DOI:10.1055/s-1998-4482

upstream raw materials:

(2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol

<2(S),3(R),4E>-2-azido-1,3-O-isopropylidene-4-octadecene-1,3-diol

(4R,5S)-5-azido-4-((E)-pentadec-1-en-1-yl)-2-phenyl-1,3-dioxane

(2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol

Downstream raw materials:

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

(2S,3R,4E)-2-Azido-1-(pivaloyloxy)-4-octadecen-3-ol

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

(2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol