N-Glycoside neoglycotrimers from 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl azide

Temelkoff, David P.; Zeller, Mat­thias; Norris, Peter

doi:10.1016/j.carres.2006.04.011

Cited by 37 publications

(28 citation statements)

References 30 publications

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“…Generally, problems arising from heterogenic phase hydrogenation can be overcome by reducing the azido group of a pentofuranuronic building block with tertiary phosphines under well-established conditions of the Staudinger reaction (Staudinger and Meyer 1919;Staudinger and Hauser 1921;Leffler and Temple 1967;Gololobov et al 1981;Gololobov 1992;Simone et al 2005;Brase et al 2005;Van Rompaey et al 2005;Temelkoff et al 2006): a method introduced for azidosugars as early as 1964 (Messmer et al 1964). The applicability of the Staudinger reaction in peptide chemistry was confirmed in the early 2000s (Saxon et al 2000;Nilsson et al 2000), and its applicability to solid phase synthesis was shown in the same year (Malkinson et al 2000;Lundquist and Pelletier 2001).…”

Section: Introductionmentioning

confidence: 99%

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

et al. 2016

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We report the solid phase synthesis of -GG-X-GG-type α/β-carbopeptoids incorporating RibAFU(ip) (1a, tX) or XylAFU(ip) (2a, cX) sugar amino acids. Though coupling efficacy is moderate, both the lengthier synthetic route using Fmoc deriva-tive (e.g., Fmoc-RibAFU(ip)-OH) and the azido deriva-tive (e.g., N 3 -RibAFU(ip)-OH) via Staudinger reaction with nBu 3 P can be successfully applied. Both X-ray dif-fraction, 1 H-and 31 P-NMR, and theoretical (QM) data support and explain why the application of Ph 3 P as Staudinger reagent is "ineffective" in the case of a cis stereoisomer, if cX is attached to the preceding residue with a peptide (-CONH-) bond. The failure of the poly-peptide chain elongation with N 3 -cX originates from the "coincidence" of a steric crowdedness and an electronic effect disabling the mandatory nucleophilic attack dur-ing the hydrolysis of a quasi penta-coordinated triph-enylphosphinimine. Nevertheless, the synthesis of the above α/β-chimera peptides as completed now by a new pathway via 1,2-O-isopropylidene-3-azido-3-deoxy-ribo-and -xylo-furanuronic acid (H-RibAFU(ip)-OH 1a and H-XylAFU(ip)-OH 2a) coupled with N-protected α-amino acids on solid phase could serve as useful examples and starting points of further synthetic efforts.

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Section: Introductionmentioning

confidence: 99%

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

et al. 2016

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“…The ease of application of this chemistry has lead to the synthesis of Nglycosyl triazole-linked oligomers such as 38 (Fig. 16) [30].…”

Section: N-glycosyl 123-triazolesmentioning

confidence: 99%

“…Reaction with a variety of glycopyranosyl azides affords good yields of amide products and allows for the synthesis of oligomeric amide-linked materials such as 21 (Fig. 8) through an iterative approach [30].…”

Section: N-glycosyl Amidesmentioning

confidence: 99%

Pyranose N-Glycosyl Amines: Emerging Targets With Diverse Biological Potential

Norris¹

2008

CTMC

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Interest in the chemistry and biological properties of non-nucleoside N-glycosidic compounds has gathered pace over the past several years; the occurrence of the N-glycoside moiety in glycoproteins and a range of active natural products has prompted the synthesis of a diverse spectrum of related materials with promising potential in medicinal chemistry. Particularly prominent has been the synthesis of novel N-glycosyl amides, 1,2,3-triazoles, and progress in the construction and diversification of natural products such as the mannopeptimycins and indolocarbazoles, each of which are discussed in this article.

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“…For background information on N-glycosidic mimics of naturally occurring carbohydrates, see: Norris (2008); Temelkoff et al (2006). For details of the synthesis of the carbohydrate starting material used, see: Zhang et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

4-Butyl-1-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-1H-1,2,3-triazole

2009

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The title compound, C18H27N3O7, was synthesized by CuI-catalysed coupling of an azide with an alkyne as part of a study into the synthesis of N-glycosyl-1,2,3-triazoles. The crystal structure confirms the selective formation of the β-conformer of the pyranose N-glycoside, thus confirming the retention of stereochemistry during heterocycle formation with the N-glycosyl triazole group occupying the equatorial position at the anomeric C atom. The structure exhibits two crystallographically independent molecules (A and B) with essentially identical conformations with a weighted r.m.s. deviation of only 0.09 Å. The molecules are arranged in layers with hydrophobic and more polar sections built from the butyl triazole units on the one hand and the more polar moieties dominated by the carbohydrate units on the other. Within the polar layers, intermolecular interactions are dominated by a three-dimensional network of weak C—H⋯O hydrogen bonds with the acetyl keto O atoms as the hydrogen-bond acceptors. The triazole units interact with each other via C—H⋯N hydrogen bonds which connect the molecules into two infinite chains of molecules made up of either A molecules or B molecules that stretch parallel to each other along [100]. Between the butyl groups no directional interactions are observed.

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N-Glycoside neoglycotrimers from 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl azide

Cited by 37 publications

References 30 publications

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

Pyranose N-Glycosyl Amines: Emerging Targets With Diverse Biological Potential

4-Butyl-1-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-1H-1,2,3-triazole

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