Glycosyl Imidates, 42 Selectively Protected Lactose and 2‐Azido Lactose, Building Blocks for Glycolipid Synthesis
1989; Wiley; Volume: 1989; Issue: 11 Linguagem: Inglês
10.1002/jlac.198919890276
ISSN0170-2041
AutoresKarl‐Heinz Jung, Monika Hoch, Richard R. Schmidt,
Tópico(s)Chemical Synthesis and Analysis
ResumoAbstract 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.
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