(2S,3S,4R)-2-aminoicosane-1,3,4-triol

Base Information

• Chemical Name: (2S,3S,4R)-2-aminoicosane-1,3,4-triol
• CAS No.: 3530-53-8
• Molecular Formula: C₂₀H₄₃NO₃
• Molecular Weight: 345.566
• Hs Code.: 2922199090
• DSSTox Substance ID: DTXSID10486639
• Metabolomics Workbench ID: 63577
• Nikkaji Number: J16.128D
• Wikidata: Q27133531
• Mol file: 3530-53-8.mol

Synonyms:C20 phytosphingosine;3530-53-8;(2S,3S,4R)-2-aminoicosane-1,3,4-triol;D-ribo C20-Phytosphingosine;(2S,3S,4R)-2-aminoeicosane-1,3,4-triol;C20-Phytosphingosine;SCHEMBL13780782;CHEBI:64910;DTXSID10486639;Q27133531

Chemical Property of (2S,3S,4R)-2-aminoicosane-1,3,4-triol

Chemical Property:

• PSA: 86.71000
• LogP: 4.59950
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 18
• Exact Mass: 345.32429423
• Heavy Atom Count: 24
• Complexity: 251

Purity/Quality:

D-riboC20-Phytosphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCC(C(C(CO)N)O)O
• Isomeric SMILES: CCCCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O
• Uses: D-ribo C20-Phytosphingosine is one of the principal sphingoid bases in plants, some fungi and marine organisms but are also present in mammalian tissues.

Technology Process of (2S,3S,4R)-2-aminoicosane-1,3,4-triol

There total 5 articles about (2S,3S,4R)-2-aminoicosane-1,3,4-triol 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: 87.0%

(2S,3S,4R,6E/Z)-2-azido-1,3,4-tri-O-benzyl-6-eicosene-1,3,4-triol → (2S,3S,4R)-2-amino-1,3,4-eicosaneanetriol (3530-53-8)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; water; for 48h; under 2250.2 Torr;

Reference yield: 86.0%

(2S,3S,4R)-2-aminoicosane-1,3,4-triol TFA salt (1335002-13-5) → (2S,3S,4R)-2-amino-1,3,4-eicosaneanetriol (3530-53-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.carres.2011.05.028

Reference yield: 80.0%

(2S,3S,4R)-2-azido-1,3,4-tri-O-benzyl-1,3,4-eicosanetriol (164988-76-5) → (2S,3S,4R)-2-amino-1,3,4-eicosaneanetriol (3530-53-8)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; water; under 2250.2 Torr;

upstream raw materials:

(2S,3S,4R)-2-azido-1,3,4-tri-O-benzyl-1,3,4-eicosanetriol

(2S,3S,4R)-2-aminoicosane-1,3,4-triol TFA salt

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