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Glycosyl Imidates, 76. Synthesis of Aryl C-Glycosides of Glucosamine

✍ Scribed by Castro-Palomino, Julio C. ;Schmidt, Richard R.

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
313 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The N‐tetrachlorophthalimido‐protected glucosamine donor 2 reacts with electron‐rich phenol ethers 3a–c to afford aryl C‐glycosides 4a–c. The N‐tetrachlorophthaloyl group could be readily removed by sodium borohydride treatment and then phthalide formation or by treatment with ethylenediamine, respectively. The resulting product was subjected to reaction with acetic anhydride in pyridine to afford N,O‐acetylated compounds 5a–c. After treatment with enthylenediamine also the N,O‐unprotected compounds could be obtained as shown for 6c.

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