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Einfache Darstellung des DL-Erythro-2-amino-octadecan-1,3-diols. 11. Mitteilung über Sphingosin und Sphingolipoide

✍ Scribed by I. Sallay; F. Dutka; G. Fodor

Publisher: John Wiley and Sons
Year: 1954
Tongue: German
Weight: 563 KB
Volume: 37
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19540370315

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✦ Synopsis

Abstract

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.

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## Abstract Sphingosine was cleaved by ozonolysis into 2‐hydroxy‐3‐aminobutyrolactone‐hydrochloride, this, in turn, hydrogenated in two steps to a slightly levorotatory 2‐amino‐1, 3,4‐butantriol. The latter proved to be the antipode of the amino‐butantriol obtained on hydrogenation of the γ‐lactone