Multigram-scale synthesis of l, d-heptoside using a Fleming-Tamao oxidation promoted by mercuric trifluoroacetate. (2nd September 2016)

• Record Type: Journal Article
• Authors: Li, Tianlei; Tikad, Abdellatif; Durka, Maxime; Pan, Weidong; Vincent, Stéphane P.
• Is Part Of: Carbohydrate research. Volume 432(2016)
• Page Start: 71
• Page End: 75
• Publication Date: 2016-09-02
• Subjects: Heptose -- Fleming-Tamao oxidation -- Homologation -- Grignard addition -- Lipopolysaccharide; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2016.07.010
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: An efficient multigram-scale synthesis of methyl 2, 3, 4, 6-tetra- O -benzyl-l - glycero -α-d - manno -heptopyranoside from methyl 2, 3, 4-tri- O -benzyl-α-d -mannopyranoside is reported. It involves a sequence of Swern oxidation, Grignard addition and Fleming-Tamao reactions. The resulting scaffold was used as a precursor to design a small library of clickablel -heptosides. This study shows that the use of mercuric bistrifluoroacetate is required both to accelerate and to cleanly perform the Fleming-Tamao oxidation, without side-reactions. Graphical abstract: Highlights: Heptosides are important bacterial carbohydrates associated with key cellular functions. Heptosides are involved in the pathogenicity and the virulence of some important infectious agents. Multi-gram scale synthesis of L, D-mannoheptose, a key component of Lipopolysaccharide. Clickable heptosides as interesting molecular tools for generating libraries of heptose mimetics. Heptose glycomimetics.