(2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyl)-1-pivaloyl-erythro-sphingosine

Base Information

• Chemical Name: (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyl)-1-pivaloyl-erythro-sphingosine
• CAS No.: 114275-42-2
• Molecular Formula: C29H57N3O3Si
• Molecular Weight: 523.87
• DSSTox Substance ID: DTXSID401105691
• Mol file: 114275-42-2.mol

Synonyms:114275-42-2;(2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyl)-1-pivaloyl-erythro-sphingosine;[(E,2S,3R)-2-azido-3-[tert-butyl(dimethyl)silyl]oxyoctadec-4-enyl] 2,2-dimethylpropanoate;Propanoic acid, 2,2-dimethyl-, 2-azido-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-octadecenyl ester, [R-[R*,S*-(E)]]- (9CI);DTXSID401105691;(2S,3R,4E)-2-Azido-3-(TBDMS)-1-pivaloyl-erythro-sphingosine;Propanoic acid, 2,2-dimethyl-, 2-azido-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-octadecenyl ester, [R-[R*,S*-(E)]]-

Chemical Property of (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyl)-1-pivaloyl-erythro-sphingosine

Chemical Property:

• Appearance/Colour: Colourless oil
• PSA: 85.28000
• LogP: 9.35506
• Solubility.: Acetone, Dichloromethane, Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 22
• Exact Mass: 523.41691922
• Heavy Atom Count: 36
• Complexity: 674

Purity/Quality:

99% ^*data from raw suppliers

(2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyl)-1-pivaloyl-erythro-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(COC(=O)C(C)(C)C)N=[N+]=[N-])O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COC(=O)C(C)(C)C)N=[N+]=[N-])O[Si](C)(C)C(C)(C)C

Technology Process of (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyl)-1-pivaloyl-erythro-sphingosine

There total 7 articles about (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyl)-1-pivaloyl-erythro-sphingosine 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: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3R,4E)-2-Azido-1-(pivaloyloxy)-4-octadecen-3-ol (114275-41-1) → (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-1-(pivaloyloxy)-4-octadecen (114275-42-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 72h; Ambient temperature;

Reference yield:

2-azido-sphingosine (103348-49-8) → (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-1-(pivaloyloxy)-4-octadecen (114275-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / pyridine / 6 h / -10 °C

2: 90 percent / imidazole / CH₂Cl₂ / 72 h / Ambient temperature

With 1H-imidazole; In pyridine; dichloromethane;

Reference yield:

(n-tetradecyl)triphenylphosphonium bromide (25791-20-2) → (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-1-(pivaloyloxy)-4-octadecen (114275-42-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) C₆H₅Li / 1.) toluene, ether; 2.) toluene, THF, ether, -30 deg C, 20 min

2: 1.) pyridine, (CF₃CO)2O, 2.) NaN₃ / 1.) CH₂Cl₂, -15 deg C, 15 min; 2.) CH₂Cl₂, DMF, room temperature, 5 h

3: 75 percent / p-TsOH / methanol; CH₂Cl₂ / 12 h / Ambient temperature

4: 75 percent / pyridine / 6 h / -10 °C

5: 90 percent / imidazole / CH₂Cl₂ / 72 h / Ambient temperature

With pyridine; 1H-imidazole; sodium azide; toluene-4-sulfonic acid; phenyllithium; trifluoroacetic anhydride; In pyridine; methanol; dichloromethane;

upstream raw materials:

tert-butyldimethylsilyl chloride

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

2-azido-sphingosine

(n-tetradecyl)triphenylphosphonium bromide

Downstream raw materials:

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