(2S,3R,4E)-2-azido-3-O-benzylsphingosine

Base Information

• Chemical Name: (2S,3R,4E)-2-azido-3-O-benzylsphingosine
• CAS No.: 130259-14-2
• Molecular Formula: C₂₅H₄₁N₃O₂
• Molecular Weight: 415.619
• Mol file: 130259-14-2.mol

Synonyms:(2S,3R,4E)-2-azido-3-O-benzylsphingosine

Chemical Property of (2S,3R,4E)-2-azido-3-O-benzylsphingosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-2-azido-3-O-benzylsphingosine

There total 4 articles about (2S,3R,4E)-2-azido-3-O-benzylsphingosine 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: 89.0%

(2S,3R,4E)-2-azido-3-benzyloxy-1-trityloxy-4-octadecene (162019-93-4) → (2S,3R,4E)-2-azido-3-O-benzylsphingosine (130259-14-2)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 90 ℃; for 24h;

Reference yield: 61.0%

(E)-(2R,3R)-3-Benzyloxy-octadec-4-ene-1,2-diol (850223-34-6) → (2S,3R,4E)-2-azido-3-O-benzylsphingosine (130259-14-2)

Guidance literature:

(E)-(2R,3R)-3-Benzyloxy-octadec-4-ene-1,2-diol; With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 0 ℃; for 3h;

With trimethylsilylazide; In dichloromethane; at 0 - 20 ℃;

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2005.01.104

Reference yield:

C28H45NO2 → (2S,3R,4E)-2-azido-3-O-benzylsphingosine (130259-14-2)

Guidance literature:

C₂₈H₄₅NO₂; With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; at 0 - 20 ℃; for 60h; Inert atmosphere;

With rochelle salt; In diethyl ether; for 0.75h; Inert atmosphere;

With copper(ll) sulfate pentahydrate; triflic azide; potassium carbonate; In methanol; water; toluene; for 3h; Inert atmosphere;

DOI:10.1002/chem.201200468

upstream raw materials:

(2S,3R,4E)-2-azido-3-benzyloxy-1-trityloxy-4-octadecene

(E)-(2R,3R)-3-Benzyloxy-octadec-4-ene-1,2-diol

2-azido-sphingosine

Downstream raw materials:

(2S,3R,4E)-2-azido-1-(4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxyoctadec-4-ene

2-deoxy-2-fluoro-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->1)-(2S,3R,E)-2-azido-3-O-benzyl-4-octadecene-1,3-diol

2-deoxy-2-fluoro-3,4,6-tri-O-benzyl-α-D-galactopyranosyl-(1->1)-(2S,3R,E)-2-azido-3-O-benzyl-4-octadecene-1,3-diol

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