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2005
Carbohydrates
U 0500
6-O-Silyl-N-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxyglucosides: Effective
Acceptors in the Glucosamine 4-OH Series. Effect of Anomeric Stereo29- 200 Glycosyl
chemistry on the Removal of the Oxazolidinone Group. — The oxazolidinone sugars (I) are found to be efficient glycosyl acceptors. The desired 1,4-disaccharides are
obtained in high yields with moderate to excellent stereoselectivity. The β-anomeric
disaccharides are able to undergo selective cleavage of the oxazolidinone ring yielding
N-acylglucosamines directly. In contrast, the corresponding α-anomers are cleared at
the oxazolidinone ring and the acetamide bond. Reacetylation is necessary to provide
the corresponding N-acylglucosamines. — (CRICH*, D.; VINOD, A. U.; J. Org.
Chem. 70 (2005) 4, 1291-1296; Dep. Chem., Univ. Ill., Chicago, IL 60607, USA;
Eng.) — Jannicke
2005
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