N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-sphingosine

Base Information

• Chemical Name: N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-sphingosine
• CAS No.: 140408-14-6
• Molecular Formula: C23H47NO4
• Molecular Weight: 401.63
• DSSTox Substance ID: DTXSID30472332
• Nikkaji Number: J1.961.145K
• Wikidata: Q82301212
• Mol file: 140408-14-6.mol

Synonyms:140408-14-6;N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-sphingosine;tert-butyl N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]carbamate;FT-0663562;DTXSID30472332

Chemical Property of N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-sphingosine

Chemical Property:

• PSA: 82.28000
• LogP: 5.91860
• Solubility.: Chloroform, Methanol
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 19
• Exact Mass: 401.35050898
• Heavy Atom Count: 28
• Complexity: 368

Purity/Quality:

N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(C(CO)NC(=O)OC(C)(C)C)O
• Isomeric SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](CO)NC(=O)OC(C)(C)C)O
• Uses: Protected D-erythro-C18-Dihydro-D-sphingosine (D449400). Biosynthetic precursor of Sphingosine. Inhibits protein kinase C.

Technology Process of N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-sphingosine

There total 12 articles about N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-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: 98.0%

(2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one (437609-37-5) → (2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> (140408-14-6)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In ethanol; at -78 ℃; for 6h;

DOI:10.1021/jo030355b

Reference yield: 97.0%

N-tert-butyloxycarbonylsphingosine (116467-63-1) → (2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> (140408-14-6)

Guidance literature:

With Rh/Al₂O₃; hydrogen; In methanol; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1016/j.ejmech.2016.08.008

Reference yield: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + 2(S)-[(1(R)-phenylethyl)amino]octadecane-1,3-diol (620161-22-0) → (2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> (140408-14-6)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 20 ℃; for 15h; under 760 Torr;

DOI:10.1021/jo034755a

upstream raw materials:

(2S,3R)-2-[(tert-butoxycarbonyl)amino]-1,2-O-N-isopropylideneoctadecane-1,3-diol

(2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one

di-tert-butyl dicarbonate

2(S)-[(1(R)-phenylethyl)amino]octadecane-1,3-diol

Downstream raw materials:

(2S,3R)-2-amino-1,3-octadecanediol