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Einfache Darstellung des DL ‐Erythro‐2‐amino‐octadecan‐1,3‐diols. 11. Mitteilung über Sphingosin und Sphingolipoide
Author(s) -
Sallay I.,
Dutka F.,
Fodor G.
Publication year - 1954
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19540370315
Subject(s) - chemistry , hydrogenolysis , hydrochloride , diastereomer , yield (engineering) , ethyl diazoacetate , derivative (finance) , stereochemistry , organic chemistry , catalysis , cyclopropanation , materials science , economics , financial economics , metallurgy
A five‐step synthesis of DL‐erythro‐2‐acetamino‐octadecan‐1,3‐diol (IXb) from palmitoic acid was realised. Palmitoic acid was converted into 2‐bromo‐palmitoylbrornide (11), this, in turn, condensed with ethyl diazoacetate into ethyl 2‐diazo‐3‐oxo‐4‐bromostearate (IV), which furnished on hydrogenolysis the hydrochloride of ethyl 2‐amino‐3‐oxo‐stearate (Vb). – The N‐acetyl derivative X of the latter afforded by the action of LiBH, N‐acetyl‐2‐amino‐l,3‐octadecandiol (IXb) in 26% yield based upon palmitoic acid.