Synthesis of a Hydroxymethylene‐Bridged Galβ(→3)Gal  c ‐Disaccharide | Zendy

Schmidt Richard R. | Zendy; Beyerbach Armin | Zendy

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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 .

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