Synthesis of O-{2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-β-d-glucopyranosyl 4-phosphate}-(1→6)-2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-d-glucose The monosaccharide route
✍ Scribed by Patricia Szabó; S.Robert Sarfati; Christian Diolez; Ladislas Szabó
- Book ID
- 107725346
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- English
- Weight
- 242 KB
- Volume
- 111
- Category
- Article
- ISSN
- 0008-6215
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📜 SIMILAR VOLUMES
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
Treatment of benzyl 2-acetamido-2-deoxy-alpha-D-galactopyranoside with 4-methoxybenzaldehyde dimethyl acetal in N,N-dimethylformamide in the presence of 4-toluenesulfonic acid afforded the 4,6-O-(4-methoxybenzylidene) acetal, which was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosy