A palladium and gold catalytic system enables direct access to O- and S-linked non-natural glyco-conjugates. Issue 48 (25th November 2016)

• Record Type: Journal Article
• Authors: Jeon, Min Ho; Mathew, Bijoy P.; Kuram, Malleswara Rao; Myung, Kyungjae; Hong, Sung You
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 48(2016)
• Page Start: 11518
• Page End: 11524
• Publication Date: 2016-11-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02437h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A Pd/Au-catalyzed Sonogashira reaction allows the direct synthesis of O - and S -linked non-natural glyco-conjugates. Abstract : Here we report a straightforward cross-coupling method for the synthesis of non-natural glycoamino acids from alkyne-bearing monosaccharides and p -iodophenylalanine. Pd/Au-catalyzed Sonogashira coupling is tolerant to both O - and S -glycosides without any epimerization. In addition, no racemization of the amino acid was observed allowing direct access to the homogeneous glyco-conjugate in a single step. Notably, this Pd/Au catalytic system presents enhanced catalytic activity than conventional Pd/Cu and Pd-only platforms, and it further enables the convergent synthesis of glycodipeptides.