79291-95-5Relevant academic research and scientific papers
Synthesis and Structural Characteristics of all Mono- And Difluorinated 4,6-Dideoxy- d - Xylo-hexopyranoses
Briggs, Edward L.,Fontenelle, Clement Q.,Kuppala, Ramakrishna,Light, Mark E.,Linclau, Bruno,Szpera, Robert,Vendeville, Jean-Baptiste,Wells, Neil J.,Wheatley, David E.
, p. 7725 - 7756 (2021/06/28)
Protein-carbohydrate interactions are implicated in many biochemical/biological processes that are fundamental to life and to human health. Fluorinated carbohydrate analogues play an important role in the study of these interactions and find application a
Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides.
Somawardhana,Brunngraber
, p. 51 - 60 (2007/10/02)
Methyl glycopyranosides reacted with diethylaminosulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. Methyl alpha-D-glycopyranosides produced 6-deoxy-6-fluoro- and 4,6-dideoxy-4,6-difluor
Fluorinated Carbohydrates. 2. Selective Fluorination of Gluco- and Mannopyranosides. Use of 2-D NMR for Structural Assignments
Card, Peter J.,Reddy, Gade S.
, p. 4734 - 4743 (2007/10/02)
Methyl and phenyl α-glucosides, or suitably protected derivatives, may be selectively fluorinated with (diethylamino)sulfur trifluoride (DAST) at the 4- or 6-position to afford the corresponding fluorinated galacto- or glucopyranoside.In contrast to the α-glucosides, the β-glucosides underwent ring fluorination at C-3 to give the 3-deoxy-3-fluoro-β-allo derivatives.High yields of primary fluorinated (C-6) products were obtained from both α- and β glucosides by use of appropriate reaction times.Use of 6-O-trityl derivatives of methyl α- and β-glucosides gave methyl 4-deoxy-4-fluoro-α-galactopyranoside (22) and methyl 3-deoxy-3-fluoro-β-allopyranoside (19), respectively.Use of 2-D NMR (COSY) for structural assignements is also described.Fluorinated p-nitrophenyl α- and β-gluco- and -galactopyranosides (such as 15) have also been prepared by the above DAST reactions. 6-O-Pivaloate esters of methyl α-gluco-and α- and β-galactopyranoside have been prepared as an acid and DAST-stable 6-O protecting group.Proof of an intramolecular fluoride-ion delivery mechanism for the SN2 displacement reaction at C-4 in methyl α-D-mannopyranoside is described.Methyl 4-amino-4,6-dideoxy-6-fluoro-α-D-glucopyranoside, methyl 6-amino-3,6-dideoxy-3-fluoro-β-D-allopyranoside, and methyl 6-amino-4,6-dideoxy-4-fluoro-α-D-talopyranoside were also prepared via the above methodology.
