256480-12-3

Upstream product

• 5285-87-0 phenyl thiocyanate 
• 38972-71-3 (E)-3-Methyl-2-dodecen-1-ol 
• 17049-49-9 octylmagnesium bromide 
• 7437-61-8 2-methyl-3,4-epoxy-1-butene 

Downstream Products

• 256480-13-4 (2R,3R,4E,8E)-1,3-di-O-benzyl-9-methyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol 
• 256480-14-5 (2S,3R,4E,8E)-2-azido-1,3-di-O-benzyl-9-methyl-7-(phenylthio)-4,8-octadecadiene-1,3-diol 
• 256480-15-6 (2S,3R,4E,8E)-2-amino-1,3-di-O-benzyl-9-methyl-7-(phenylthio)-4,8-octadecadiene-1,3-diol 

Relevant academic research and scientific papers

Synthesis of (2S,3R,4E,8E)-9-methyl-4,8-sphingadienine via a novel S(N)2' type reaction mediated by a thioether carbanion

A stereoselective synthesis of sphingadienine 3 as a new analogue of sphingosine has been achieved by a novel copper, catalyzed S(N)2' type homoallylic coupling reaction between an allylic mesylate and a thioether- stabilized allylic carbanion.

General and efficient syntheses of C18-4,8-sphingadienines via S(N)2'-type homoallylic coupling reactions mediated by thioether-stabilized copper reagents

The stereoselective syntheses of C18-4,8-sphingadienines 3 and 4 as analogues of sphingosine 1 are described. The key step in these syntheses involved a novel S(N)2'-type homoallylic coupling reaction between the corresponding thioether-stabilized allylic copper reagents and the allylic mesylate 7. The thioether-stabilized allylic copper reagents were easily prepared and retained the configuration of their double bond during the coupling reactions, thus overcoming the problem of isomerization which was normally associated with the use of allylic organometallic reagents in such applications.