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Glycosyl Imidates, 42 Selectively Protected Lactose and 2‐Azido Lactose, Building Blocks for Glycolipid Synthesis
Author(s) -
Jung KarlHeinz,
Hoch Monika,
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.198919890276
Subject(s) - regioselectivity , chemistry , glycosyl , lactose , alkylation , derivative (finance) , disaccharide , glycolipid , protecting group , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , catalysis , alkyl , financial economics , economics
Performing regioselective alkylation at 3′‐OH of benzyl β‐lactoside 1 by the stannylation method we prepared the 3′‐OH‐ and 4′‐OH‐unprotected lactose derivatives 5 and 10 and the 4′‐OH‐unprotected lactose derivative 9 containing a different protecting group at 3′‐OH, suitable for further transformations. These building blocks are valuable glycosyl acceptors in glycolipid synthesis. For the synthesis of glycosyl donors with Gal(β1 → 4)GlcNAc‐structure we used the 2‐azido lactose derivative 19 . By regioselective alkylation of 3′‐OH by the stannylation method and application of other common regioselective protecting procedures we prepared the trichloroacetimidates 17, 24 , and 30 containing special protecting groups at 3′‐OH, 4′‐OH, and 6′‐OH which are suitable for further transformations in these positions.