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

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 a...

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Veröffentlicht in:Liebigs Annalen 1997-05, Vol.1997 (5), p.859-863
Hauptverfasser: Mayer, Thomas G., Schmidt, Richard R.
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0947-3440
1099-0690
DOI:10.1002/jlac.199719970511