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Glycosyl Imidates, 74. Synthesis of Ganglioside GM 1 via a GM 3 Intermediate
Author(s) -
Greilich Ulrike,
Brescello Roberto,
Jung KarlHeinz,
Schmidt Richard R.
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960504
Subject(s) - chemistry , glycosyl , acetylation , glycosylation , ganglioside , lactose , stereochemistry , glycosyl donor , acceptor , biochemistry , gene , physics , condensed matter physics
The synthesis of GM 1 ( 1 ) via GM 3 intermediate 7 was based on lactose building‐block 5 , sialyl donors 6 , and a Galß(1–3)‐GalN 3 donor 13α . Reaction of donor 13α with acceptor 7 in the presence of TMSOTf as catalyst afforded GM 1 pentasaccharide 30 . Azido group reduction, N ‐acetylation, hydrogenolytic O ‐debenzylation, and O ‐acetylation furnished O ‐acyl‐protected GM 1 pentasaccharide 34 . Chemoselective 1a‐ O ‐deacetylation and generation of O ‐(pentaosyl)trichloro‐acetimidate 36 provided the required glycosyl donor for the application to azidosphingosine glycosylation procedure affording GM 1 ( 1 ).