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Synthesis of a Hydroxymethylene‐Bridged Galβ(→3)Gal c ‐Disaccharide
Author(s) -
Schmidt Richard R.,
Beyerbach Armin
Publication year - 1992
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.1992199201161
Subject(s) - disaccharide , chemistry , electrophile , yield (engineering) , derivative (finance) , aldehyde , raney nickel , stereochemistry , organic chemistry , hydrogen , catalysis , materials science , economics , financial economics , metallurgy
Direct lithiation of the readily available 2‐phenylsulfinyl‐ D ‐galactal 3S furnishes with aldehyde 8 as electrophile in a diastereocontrolled reaction the C ‐disaccharide intermediate 9 . Subsequent removal of the phenylsulfinyl group with Raney nickel and diastereospecific 2b‐hydrogen and 3b‐hydroxy transfer provide the β(1→3)‐connected C ‐disaccharide 11 in high yield. The structure of 11 was deduced from its derivative 12 on the basis of 1 H‐NMR data. Hydrogenolytic O ‐debenzylation gives compound 13 , which is characterized as O ‐acetylated compound 14 .