207516-23-2

Usage

Chemical Properties

Colourless Oil

Uses

A protected Sphingosine

InChI:InChI=1/C26H49NO4/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23-22(21-28)27(26(5,6)30-23)24(29)31-25(2,3)4/h19-20,22-23,28H,7-18,21H2,1-6H3/b20-19+/t22?,23-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 207516-20-9 Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester 
• 263543-27-7 C₄₂H₆₇NO₄Si 
• 77-76-9 2,2-dimethoxy-propane 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 

Downstream Products

• 1200446-75-8 C₆₀H₇₅NO₁₃ 
• 1200446-78-1 C₆₀H₇₅NO₁₃ 
• 1196664-99-9 (4S,5R,1''E)-tert-butyl-4-((((4'-bromo-5'-methoxy-2'-nitrophenyI)(phenyl)methoxy)(methoxy)phosphoryloxy)methyI)-2,2-dimethyl-5-(pentadec-1''-enyl)oxazolidine-3-carboxylate 
• 1196664-91-1 tert-butyl (4S,5R,1''E)-4-((((4'-bromo-5'-hydroxy-2'-nitrophenyl)(phenyl)methoxy)(hydroxy)phosphoryloxy)methyl)-2,2-dimethyl-5-(pentadec-1''-enyl)oxazolidine-3-carboxylate 
• 1196665-00-5 tert-butyl (4S,5R,1E)-4-((((4'-bromo-5'-methoxy-2'-nitrophenyl)(phenyl)methoxy)(methoxy)phosphoryloxy)methyl)-2,2-dimethyl-5-(pentadec-1-enyl)oxazolidine-3-carboxylate 
• 1196665-02-7 (4'-bromo-5'-hydroxy-2'-nitrophenyl)(phenyl)methyl-(2S,3R,4E)-3-hydroxy-2-palmitamidooctadec-4-enyl hydrogen phosphate 
• 1196665-01-6 (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-enyl-(4'-bromo-5'-hydroxy-2'-nitrophenyl)(phenyl)methyl hydrogen phosphate 
• 207516-26-5 (4S,5R)-4-{Bis-[1-(2-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 207516-11-8 Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester bis-[1-(2-nitro-phenyl)-ethyl] ester 
• 26993-30-6 Sphingosine-1-phosphate 

Relevant academic research and scientific papers

CAGED CERAMIDE-1-PHOSPHATE DERIVATIVES

The invention relates to novel caged ceramide 1-phosphate (C1P) and the method of using them for delivering C1P intracellularly in vitro and in vivo, for research and therapeutic purposes.

A properly protected sphingosine acceptor for helferich glycosylation

The synthesis and some examples of glycosylations of a properly protected sphingosine is presented. This compound is suitable for the preparation of glycosphingolipids. It has been used for the synthesis of -mannosylceramide and sulfatide exploiting the anchimeric assistance to address the stereochemistry of the glycosidic bond.

Caged ceramide 1-phosphate analogues: Synthesis and properties

(Chemical Equation Presented) Sphingolipid phosphate analogues bearing 7-(diethylamino)-coumarin (DECM) and 4-bromo-5-hydroxy-2-nitrobenzhydryl (BHNB) groups in a photolabile ester bond were synthesized. The ability of the "caged" ceramide 1-phosphate analogues to release the bioactive parent molecule upon irradiation at 400-500 nm was demonstrated by stimulation of macrophage cell proliferation. 2009 American Chemical Society.

Synthesis and evaluation of a photolyzable derivative of sphingosine 1-phosphate-caged SPP

The synthesis of a photolyzable sphingosine 1-phosphate derivative is reported via the reaction of N-(tert-butoxycarbonyl)-2-N,3-O-isopropylidenesphingosine 7 and bis(α-methyl-o-nitrobenzyl) N,N-diisopropylphosphoramidite. Stimulation of DNA synthesis upon illumination of caged SPP-loaded cells is also described.