76604-30-3Relevant academic research and scientific papers
Sphingolipids: Part III - Synthesis of 2-Amino-1,3-dihydroxydodecane (C12-Dihydrosphingosine)
Turel, R. J.,Manerikar, S. V.,Kulkarni, A. B.
, p. 676 - 678 (2007/10/02)
The four-step synthesis of the title compound involves: (i) condensation of decanoyl chloride with ethyl sodioacetoacetate to give ethyl decanoylacetoacetate (I); (ii) Japp-Klingemann reaction of I with p-nitrophenyldiazonium chloride to give ethyl (2-nitrophenylhydrazono)-2,3-dioxododecanoate (II); (iii) reductive acetylation of II with zinc, acetic acid and acetic anhydride furnishing ethyl 2-acetamido-3-oxododecanoate (VI); and (iv) NaBH4-MgCl2 reduction of VI followed by hydrolysis (KOH) of the resulting 2-acetamido-1,3-dihydroxydodecanoate (VIII) to give 2-amino-1,3-dihydroxydodecane (C12-DHS) (IX).
