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Glycosyl Imidates, 43 Synthesis of Lacto neo tetraosyl Ceramide
Author(s) -
Bommer René,
Schmidt Richard R.
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890277
Subject(s) - chemistry , glycosylation , ceramide , glycosyl donor , tetrasaccharide , stereochemistry , palmitoylation , derivative (finance) , glycosyl , sphingosine , acceptor , combinatorial chemistry , organic chemistry , biochemistry , polysaccharide , cysteine , financial economics , economics , apoptosis , physics , receptor , enzyme , condensed matter physics
Azidosphingosine glycosylation proved to be a valuable method for the synthesis of lacto neo tetraosyl ceramide 15 . For this aim the 2‐azido‐2‐deoxylactosyl donor 5 was treated with the lactosederived acceptor 4 to provide the tetrasaccharide derivative 6 . Transformation into the corresponding trichloroacetimidate 10 led to an efficient tetraosyl donor for the β‐selective glycosylation of 3‐ O ‐benzoyl‐azidosphingosine 11 . The product 12 was converted into the lysoglycosphingolipid 14 ; palmitoylation of the free amino group then afforded compound 15 .