Gold(i)-promoted α-selective sialylation of glycosyl ortho-hexynylbenzoates for the latent-active synthesis of oligosialic acids. Issue 27 (26th June 2019)

• Record Type: Journal Article
• Authors: Wang, Jiazhe; Lou, Qixin; Rong, Jingjing; Yang, You
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 27(2019)
• Page Start: 6580
• Page End: 6584
• Publication Date: 2019-06-26
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00954j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A gold(i )-promoted α-selective glycosylation approach with sialyl ortho -hexynylbenzoates as donors is developed for the latent-active synthesis of α-(2 → 9)-linked oligosialic acids. Abstract : A gold(i )-promoted α-selective sialylation approach with 5- N, 4- O -oxazolidinone-protected sialyl ortho -hexynylbenzoates as donors is described for the stereoselective synthesis of α-sialosides. Iterative couplings of the 'active' sialyl ortho -hexynylbenzoates and the 'latent' sialyl ortho -iodobenzoates provide a new approach for the 'latent-active' synthesis of α-(2 → 9)-linked oligosialic acids that are relevant to N. meningitidis serogroup C capsular polysaccharide.