N-(tert-Butoxycarbonyl)-3-O-benzoylsphingosine

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-3-O-benzoylsphingosine
• CAS No.: 299172-59-1
• Molecular Formula: C30H49NO5
• Molecular Weight: 503.723
• DSSTox Substance ID: DTXSID801119658
• Nikkaji Number: J1.643.537F
• Mol file: 299172-59-1.mol

Synonyms:DTXSID801119658;N-(tert-Butoxycarbonyl)-3-O-benzoylsphingosine;1,1-Dimethylethyl N-[(1S,2R,3E)-2-(benzoyloxy)-1-(hydroxymethyl)-3-heptadecen-1-yl]carbamate

Chemical Property of N-(tert-Butoxycarbonyl)-3-O-benzoylsphingosine

Chemical Property:

• Boiling Point: 616.4±55.0 °C(Predicted)
• PKA: 11.29±0.46(Predicted)
• PSA: 84.86000
• Density: 1.018±0.06 g/cm3(Predicted)
• LogP: 7.74580
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 21
• Exact Mass: 503.36107366
• Heavy Atom Count: 36
• Complexity: 607

Purity/Quality:

97% ^*data from raw suppliers

(2S,3R,4E)-3-Benzoyl-2-tert-butyloxycarbonylamino-4-octadecen-1,3-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(CO)NC(=O)OC(C)(C)C)OC(=O)C1=CC=CC=C1
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)OC(C)(C)C)OC(=O)C1=CC=CC=C1

Technology Process of N-(tert-Butoxycarbonyl)-3-O-benzoylsphingosine

There total 8 articles about N-(tert-Butoxycarbonyl)-3-O-benzoylsphingosine 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: 54.0%

tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate (263558-18-5) → N-(tert-butoxycarbonyl)-3-O-benzoyl-D-erythro-sphingosine (299172-59-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; ethanol; at 20 ℃; for 20h;

DOI:10.1002/ejoc.201500025

Reference yield: 43.0%

tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate (263558-18-5) → 3-O-benzoyl-D-erythro-sphingosine (4201-60-9) + N-(tert-butoxycarbonyl)-3-O-benzoyl-D-erythro-sphingosine (299172-59-1)

Guidance literature:

With trifluoroacetic acid; for 3h;

DOI:10.1039/b002104k

Reference yield:

tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (115464-03-4) → N-(tert-butoxycarbonyl)-3-O-benzoyl-D-erythro-sphingosine (299172-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / pyridine; DMAP / 2 h

2: 43 percent / trifluoroacetic acid / 3 h

With pyridine; dmap; trifluoroacetic acid; 1: Mitsunobu reaction;

DOI:10.1039/b002104k

upstream raw materials:

tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate

(4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester

tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

benzoic acid

Downstream raw materials:

(2S,3R,E)-3-O-benzoyl-2-(tert-butoxycarbonyl)amido-1-(tert-butyldiphenylsilyloxy)-4-octadecene-1,3-diol

N-tert-butyloxycarbonylsphingosine

glucosylceramide

C₅₈H₇₇NO₁₁