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Muramic acid derivatives as glycosyl donors for the synthesis of muramyl-containing glycosphingolipids and fatty acids

✍ Scribed by Alexander Toepfer; Richard R. Schmidt

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 927 KB
Volume: 202
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(90)84080-e

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✦ Synopsis

2-Azido-2-deoxy-4,6-O-isopropylidene-3-O-[(lR)-(methoxycarbonyl)ethyl]-a-D-glucopyranosyl tiichloroacetimidate (3a) has been used as the glycosyl donor in the synthesis of glycosphingolipids 14 and 27. Reaction of3a with (25,3R, 4E)-2-azido-3-benzoyloxy-4-octadecen-l-01 (6) gave (2s. 3R, 4E)-2-azido-l-{2-azido-2-deoxy-4,6-0-isopropylidene-3-0-[( 1 R)-l-(methoxycarbonyl)ethyl]-~-D-glucopyranosyloxyl}-3-benzoyloxy+octadecene (7), which was converted into (2S, 3R, 4E)-I-{2-deoxy-2-hexadecanoylamino-3-O-[(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl]-B-D-glucopyranosyloxy}-2-hexadecanoylamino-4-octadecen-3-ol(l4).

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