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2‐Deoxyglycosyl fluorides in oligosaccharide synthesis
Author(s) -
Jünnemann Josef,
Lundt Inge,
Thiem Joachim
Publication year - 1991
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.1991199101130
Subject(s) - chemistry , glycosyl , fluoride , yield (engineering) , stereoselectivity , catalysis , lewis acids and bases , solvent , organic chemistry , lewis acid catalysis , glycoside , inorganic chemistry , materials science , metallurgy
3,4‐Di‐ O ‐acetyl‐2,6‐dibromo‐2,6‐dideoxy‐α‐ D ‐mannopyranosyl fluoride ( 1 ) was treated with Lewis acid catalysts to give α‐glycosides exclusively. Reactions with α‐ and β‐glucosyl analogs yield α/β mixtures under the same conditions. With no assistance of anchimeric substituents at C‐2 the stereoselectivity is directed by a glycosyl fluoride/catalyst/solvent complex. As shown in the 2‐deoxy‐ arabino ‐hexopyranosyl series this leads to improved α/β ratios and yields.