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

✍ Scribed by Mayer, Thomas G. ;Schmidt, Richard R.

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
575 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

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.

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## Abstract Reaction of 2‐__O__‐acetyl‐protected __O__‐galactosyl trichloroacetimidate 3 as glycosyl donor and 2,4‐di‐__O__‐unprotected xylopyranoside 2 as glycosyl acceptor furnished in the presence of Et~2~O · BF~3~ as catalyst regioselectively β‐(1→4)‐connected disaccharide 4 which gave upon sub