Glycosyl Imidates, 78. An Efficient Synthesis of Galactinol and Isogalacatinol

This is the authors' abstract. We don't add key points for this paper.

Abstract 2:3,4:5‐Di‐ O ‐cyclohexylidene‐ D ‐/ L ‐ myo ‐inositol ( 2 ) could be readily converted into 6‐ O ‐ and 1‐ O ‐unprotected L ‐ and D ‐ myo ‐inositol derivatives L ‐ and D ‐ 4 and L ‐ and D ‐ 6 , respectively. Their reaction with trichloroacetimidate 7 as galactosyl donor in the presence of tin(II) trifluoromethanesulfonate as catalyst afforded the desired α(1–6)‐ and α(1–1)‐connected galactopyranosides 8, 11 and 12 . Compound 11 could be readily deprotected to afford target molecule (galactinol) 1 in high overall yield; from 12 , the diastereoisomer 13 was obtained.