✦ LIBER ✦

A convenient synthesis of 2-deoxy-2-[(R)-1-hydroxytetradecanamido]-3-O-[(R)-3-hydroxytetradecanoyl]-α-d-glucopyranose 1-phosphate (lipid X)

✍ Scribed by Ingolf Macher

Publisher: Elsevier Science
Year: 1987
Tongue: English
Weight: 417 KB
Volume: 162
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(87)80202-1

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✦ Synopsis

The crystalline tris(hydroxymethyl)ainomethane ("Tris") salt of 2-deoxy-2-[(R)-3-hydroxytetradecanamido]-3-0-[(R)-3-hydroxytetradecanoyl]-cY-D-glucopyranose 1 -phosphate (lipid X) has been synthesised from 2-animo-2-deoxy-D-glucose hydrochloride in five steps in -50% overall yield. The key step was 1-0-(dibenzyl) phosphorylation of 4,6-0-benzylidene-2-[(~)-3-benzyloxytetradecanamido]-2-deoxy-n-glucopyranose, catalysed by butyl-lithium. The product was then 3-(&3benzyloxytetradecanoylated, and the benzyl and benzylidene groups were removed by catalytic hydrogenation.

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