56926-53-5Relevant articles and documents
TRACERS FOR MONITORING THE ACTIVITY OF SODIUM/GLUCOSE COTRANSPORTERS IN HEALTH AND DISEASE
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, (2010/02/16)
Radiolabeled tracers for sodium/glucose cotransporters (SGLTs), their synthesis, and their use are provided. The tracers are methyl or ethyl pyranosides having an equatorial hydroxyl group at carbon-2 and a C1 preferred conformation, radio-labeled with 18F, 123I, or 124I, or free hexoses radiolabeled with 18F, 123I, or 124I. Also provided are in vivo and in vitro techniques for using these and other tracers as analytical and diagnostic tools to study glucose transport, in health and disease, and to evaluate therapeutic interventions.
Synthesis and n.m.r. spectra of methyl 2-deoxy-2-fluoro- and 3-deoxy-3-fluoro-alpha- and beta-D-glucopyranosides.
Kovac,Yeh,Glaudemans
, p. 23 - 34 (2007/10/02)
Methyl 3-deoxy-3-fluoro-alpha- and beta-D-glucopyranosides and alpha- and beta-D-glucofuranosides were prepared by methanolysis of 3-deoxy-3-fluoro-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose. Crystalline 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-alpha-D-
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.