N-Boc sphingosine

Base Information

• Chemical Name: N-Boc sphingosine
• CAS No.: 116467-63-1
• Molecular Formula: C23H45NO4
• Molecular Weight: 399.615
• DSSTox Substance ID: DTXSID90449429
• Nikkaji Number: J1.218.649E,J1.627.154C
• Wikidata: Q82268890
• Mol file: 116467-63-1.mol

Synonyms:N-Boc sphingosine;116467-63-1;N-Boc-erythro-sphingosine;tert-butyl N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate;n-boc-sphingosine;SCHEMBL12451652;N-tert-butoxycarbonyl sphingosine;DTXSID90449429;UMUDVBSIURBUGW-BWMVHVDHSA-N;N-(tert-Butoxycarbonyl)sphingosine;N-tert-butyloxycarbonyl-sphingosine;BP-29812;(2S,3R)-2-(tert-Butyloxycarbonylamino)-4-octadecene-1,3-diol

Chemical Property of N-Boc sphingosine

Chemical Property:

• PSA: 82.28000
• LogP: 5.69460
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 18
• Exact Mass: 399.33485892
• Heavy Atom Count: 28
• Complexity: 404

Purity/Quality:

98% ^*data from raw suppliers

N-Boc-erythro-sphingosine ^*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)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)OC(C)(C)C)O
• Uses: The N-Boc protected Sphingosine, a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes.

Technology Process of N-Boc sphingosine

There total 56 articles about N-Boc 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: 100.0%

(2S,3S,4E)-2-N-tert-butoxycarbonylaminooctadec-1,3-O-di-(tert-butyl)silanediyl-4-ene-1,3-diol (498541-36-9) → N-tert-butyloxycarbonylsphingosine (116467-63-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(02)01807-5

Reference yield: 99.0%

tert-butyl ((2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-octadec-4-en-2-yl)carbamate (221455-36-3) → N-tert-butyloxycarbonylsphingosine (116467-63-1)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 0.5h;

DOI:10.1021/ol070991m

Reference yield: 97.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyloxycarbonylsphingosine (116467-63-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 0.5h; Ambient temperature;

DOI:10.1016/S0960-894X(97)00047-4

upstream raw materials:

tert-butyl (1S,2R)-N-<2-hydroxy-1-(hydroxymethyl)-3-heptadecynyl>carbamate

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

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

di-tert-butyl dicarbonate

Downstream raw materials:

Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester

2,2-Dimethyl-propionic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester

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

(2S,3R,E)-1-(tert-butyldiphenylsilyloxy)-2-(N-tertbutyloxycarbonyl)aminooctadec-4-en-3-ol

Refernces

• 1、 Azuma, Hideki,Takao, Ryoko,Shikata, Keiji,Niiro, Hayato,Tachibana, Taro,Ogino, Kenji. "Synthesis and potent antileukemic activities of N-lactylsphingosine and N-lactyldihydrosphingosine". . p. 3445 - 3447. Retrieved 2003.
• 2、 -. "4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO". Page/Page column 308. . Retrieved 2021/07/10.
• 3、 Aglar, ?znur,Arenz, Christoph,Banhart, Sebastian,Cong, Xiaojing,Hamdo, Housam H.,Heuer, Dagmar,Kleuser, Burkhard,M?ller, Heiko M.,Saied, Essa M.,Samaha, Doaa,Schumacher, Fabian. "Liposomal FRET Assay Identifies Potent Drug-Like Inhibitors of the Ceramide Transport Protein (CERT)". supporting information. p. 16616 - 16621. Retrieved 2020/11/30.