Stereoselective Glycosidic Coupling Reactions of Fully Benzylated 1,2-Anhydro Sugars withN-Tosyl- orN-Benzyloxycarbonyl-l-serine Methyl Ester
- 1 April 1995
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 14 (3) , 341-352
- https://doi.org/10.1080/07328309508002076
Abstract
The glycosidic coupling reaction of 1,2-anhydro-3,4,6-tri-O-benzyl-β-d-mannopyranose (7), 1,2-anhydro-3,4,6-tri-O-benzyl-α-d-galactopyranose (21), and 1,2-anhydro-3,4-di-O-benzyl-α-d-xylopyranose (18) with N-tosyl- (10) or N-benzyloxycarbonyl- (11) L-serine methyl ester provides a new stereocontrolled synthesis of 1,2-trans linked glycopeptides. The 1,2-anhydro sugars are shown to react smoothyl with 10 or 11 in the presence of Lewis acid (ZnCl2 or AgOTf) as well as powdered 4A molecular sieves in CH2Cl2 at room temperature to afford glycosyl serine derivatives with high stereoselectivity and high yield in less than 30 min. An improved method using 2-O-acetyl-3,4,6-tri-O-benzyl-α-d-mannopyranosyl chloride (6) as the key intermediate for ring closure was applied for the synthesis of 1,2-anhydro-3,4,6-tri-O-benzyl-β-d-mannopyranose.Keywords
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