Synthesis of galactofuranose-containing disaccharides using thioimidoyl-type donors

Euzen, Ronan; Ferrières, Vincent; Plusquellec, Daniel

doi:10.1016/j.carres.2006.10.001

Cited by 20 publications

(23 citation statements)

References 57 publications

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“…[100] Thioimidate donors have also been activated chemoselectively in the synthesis of sialosides [101] and galactofuranosides. [102] Overall, glycosyl thioimidates are good glycosyl donors for which interesting applications have been found in oligosaccharide synthesis. As is the case for most glycosyl donors, a reduction in the required amount of the promoter should be the focus of future research.…”

Section: Glycosyl Thioimidatesmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

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Section: Glycosyl Thioimidatesmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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“…1 H, 13 C, 31 P, 19 F, HMQC and COSY NMR spectra were recorded on a Bruker ARX 400 spectrometer at 400 MHz for 1 H, 100 MHz for 13 C, 162 MHz for 31 P and 376 MHz for 19 F. Chemical shifts are given in δ units (ppm) measured downfield from Me 4 Si. HPLC purifications were performed on a Thermo SpectraSYSTEM P1000XR instrument.…”

Section: Methodsmentioning

confidence: 99%

“…[10,11] Recently we have developed a versatile chemical method for the synthesis of natural nucleotidefuranose and analogues, [12] starting from unprotected but stable furanosyl thioimidates as donors. [13,14] This allowed us to obtain some UDP-1,2-trans-furanoses for the first time, as well as their 1,2-cis diastereoisomers, in very short reaction times and without any observation of ring expansion. Alternatively, enzymatic syntheses of 1α have also been reported.…”

Section: Introductionmentioning

confidence: 98%

Stereoselective Chemoenzymatic Synthesis of UDP‐1,2‐cis‐furanoses from α,β‐Furanosyl 1‐Phosphates

Peltier¹,

Guégan²,

Daniellou³

et al. 2008

Eur J Org Chem

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The biosynthesis of furanosyl‐containing glycoconjugates is poorly described, mainly due to the lack of UDP‐furanoses. Here we present our effort to synthesize rare nucleotide‐sugars with the aid of a multiple‐enzyme system, notably including galactose‐1‐phosphate uridylyltransferase. Firstly, STD‐NMR techniques were used to probe the broad substrate specificity of this particular enzyme. The chemical synthesis of the needed furanosyl 1‐phosphate starting materials was then performed with unprotected thioimidoyl donors. This led to the first stereoselective chemoenzymatic syntheses of UDP‐β‐L‐arabinofuranose, UDP‐α‐D‐fucofuranose and UDP‐α‐D‐6F‐galactofuranose from starting mixtures of sugar‐phosphates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…[9] The chemical lability of the Bn-protected phosphate group in this N-glycan system forced us to pursue the seemingly riskier late-stage phosphorylation strategy. Accordingly, chitobiose 3 [10] was prepared from the easily accessible benzylidene-protected glucosamine thioether donor 1 and glucosamine acceptor 2 under promotion by MeOTf (Tf = triflate, Scheme 2). Glycosylation of mannose sulfoxide donor 4 and the chitobiose acceptor under Crich-Kahne conditions gave the desired trisaccharide intermediate in satisfying yield and b-selectivity.…”

mentioning

confidence: 99%