Chemical investigations in the synthesis of O-serinyl aminoribosides

Ginisty, Maryon; Gravier‐Pelletier, Christine; Merrer, Yves Le

doi:10.1016/j.tetasy.2005.11.019

Cited by 30 publications

(14 citation statements)

References 44 publications

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“…Recently, Merrer and co-workers reported O -ribosylations of primary alcohols using bromo- or fluoro-ribosides with the established promoters such as AgOTf or SnCl 2 /AgClO 4 10. Reaction rates for O -ribosylations with 1-halo riboside are very slow (6~36h), and in our hands under these conditions O -ribosylations of the secondary alcohols resulted in unsatisfactory yields of 15~65%.…”

mentioning

confidence: 60%

Highly Efficient O-Glycosylations with p-Tolyl Thioribosides and p-TolSOTf

Kurosu

2008

J. Org. Chem.

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A wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1~15 min. to provide the desired products in good yield with reliable α/β selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosamino-uridine library molecules in solution or on polymer-support.The 5-deoxy-5-aminoribose moiety of ribosamino-uridine antibiotics (i.e. muraymycin, liposidomycin, caprazamycin, and FR-900493) has been considered as an important functional group to exhibit excellent antibacterial activities. 1 These antibiotics are known to interfere with the enzyme involved in the committed step of peptidoglycan biosynthesis, MraY which catalyzes the transformation of UDP-N-acylmuramyl-L-alanyl-γ-D-glutamyl-mesodiaminopimelyl-D-alanyl-D-alanine (Park's nucleotide) to prenylpyrophosphoryl-Nacylmuramyl-L-Ala-γ-D-glu-meso-DAP 2 -D-Ala-D-Ala (lipid I), and are non-toxic or less toxic in vivo. Thus, MraY has been a target of interest for the discovery of novel antimycobacterial agents. 3 However, medicinal chemistry programs of these natural products with an aim to improve the efficacy including pharmacokinetics are hampered by a limited number of modification reactions which can selectively modify the desired positions of such complex molecules. 4 In addition, one of the drawbacks of performing medicinal chemistry with these complex antibiotics is the requirement for the fermentation of the natural product starting materials. 5 michio.kurosu@colostate.edu. In our ongoing effort to define the minimum structure requirement of ribosamino-uridine MraY inhibitors of natural product origin to exhibit equal biological activity, 6 we envisioned synthesizing a library of ribosamino-uridine molecules in solution or on polymer-support. 7 Because structural diversity of ribosamino-uridine antibiotics are observed not only in the lipid moiety (R group in Figure 1) but also at the 2-position of aminoribose moiety (i.e. methyl or sulfonyl group), it is desired to develop a versatile and robust ribosylation method which also amenable to glycosylations on polymer-support. 8 Although numerous examples of N-glycosylations of purine or pyrimidine bases with furanose derivatives have been reported, 9 O-ribosylation has rarely discussed in literatures. Recently, Merrer and co-workers reported O-ribosylations of primary alcohols using bromo-or fluororibosides with the established promoters such as AgOTf or SnCl 2 /AgClO 4 . 10 Reaction rates for O-ribosylations with 1-halo riboside are very slow (6~36h), and in our hands under these conditions O-ribosylations of the secondary alcohols resulted in unsatisfactory yields of 15~65%. In addition, because of the limited accessibility of 1-halo ribosides it is difficult to diversify ribosami...

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confidence: 60%

Highly Efficient O-Glycosylations with p-Tolyl Thioribosides and p-TolSOTf

Kurosu

2008

J. Org. Chem.

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“…[16][17][18][19] We chose as starting materials the carbohydrates D-glucose, D-mannose, D-ribose, and D-galactose in order to obtain aldehydes 1-4 with varied substitution patterns and, more importantly, with different stereochemistry. The initial studies for the arylation reaction focused on optimization of the reaction conditions using phenylboronic acid and aldehyde 1, derived from D-glucose.…”

Section: Resultsmentioning

confidence: 99%

“…Aldehydes 1-4 were prepared from D-glucose, D-mannose, D-ribose, and D-galactose, respectively, according to literature procedures. [16][17][18][19] Aryl-Transfer Reaction to Aldehyde 1; General Procedure In an atmosphere of argon, 1.5 M Et 2 Zn in toluene (2.33 mL, 3.6 mmol, 7.2 equiv) was slowly added to a soln of arylboronic acid (1.2 mmol, 2.4 equiv) in anhyd toluene (2 mL). The mixture was stirred at 60°C for 1 h and after this period, cooled to r.t. and a soln of the aldehyde (0.139 g, 0.5 mmol) was added.…”

Section: Resultsmentioning

confidence: 99%

Boron-Zinc Exchange in The Diastereoselective Arylation of Sugar-Based Aldehydes: Stereoselective Synthesis of (+)-7-epi-Goniofufurone and Analogues

et al. 2013

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“…Encouraged by this result we tried the substitution on the sterically more hindered tert-butyl bromide. Finally, this reaction took place in excellent yield using a large excess of tert-butyl bromide and potassium carbonate in the presence of one equivalent of triethylbenzylammonium chloride (TEBAC) used to generate a looser and more reactive ion pair (Ginisty et al 2006) (Scheme 2).…”

Section: Cbz/tert-butyl Protectionmentioning

confidence: 99%

Synthesis of protected enantiopure (R) and (S)-α-trifluoromethylalanine containing dipeptide building blocks ready to use for solid phase peptide synthesis

et al. 2016

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Considering the increasing importance of fluorinated peptides, the development of efficient and reliable synthetic methods for the incorporation of unnatural fluorinated amino acids into peptides is a current matter of interest. In this study, we report the convenient Boc/benzyl and Cbz/tert-butyl protection of both enantiomers of the quaternarized amino acid α-trifluoromethylalanine [(R)- and (S)-α-Tfm-Ala]. Because of the deactivation of the nitrogen atom of this synthetic amino acid by the strong electron withdrawing trifluoromethyl group, the peptide coupling on this position is a challenge. In order to provide a robust synthetic methodology for the incorporation of enantiopure (R)- and (S)-α-trifluoromethylalanines into peptides, we report herein the preparation of dipeptides ready to use for solid phase peptide synthesis. The difficult peptide coupling on the nitrogen atom of the α-trifluoromethylalanines was performed in solution phase by means of highly electrophilic amino acid chlorides or mixed anhydrides. The synthetic effectiveness of this fluorinated dipeptide building block strategy is illustrated by the solid phase peptide synthesis (SPPS) of the Ac-Ala-Phe-(R)-α-Tfm-Ala-Ala-NH2 tetrapeptide.

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Chemical investigations in the synthesis of O-serinyl aminoribosides

Cited by 30 publications

References 44 publications

Highly Efficient O-Glycosylations with p-Tolyl Thioribosides and p-TolSOTf

Highly Efficient O-Glycosylations with p-Tolyl Thioribosides and p-TolSOTf

Boron-Zinc Exchange in The Diastereoselective Arylation of Sugar-Based Aldehydes: Stereoselective Synthesis of (+)-7-epi-Goniofufurone and Analogues

Synthesis of protected enantiopure (R) and (S)-α-trifluoromethylalanine containing dipeptide building blocks ready to use for solid phase peptide synthesis

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Chemical investigations in the synthesis of O-serinyl aminoribosides

Cited by 30 publications

References 44 publications

Highly Efficient O-Glycosylations with p-Tolyl Thioribosides and p-TolSOTf

Highly Efficient O-Glycosylations with p-Tolyl Thioribosides and p-TolSOTf

Boron-Zinc Exchange in The Diastereoselective Arylation of Sugar-Based Aldehydes­: Stereoselective Synthesis of (+)-7-epi-Goniofufurone and Analogues

Synthesis of protected enantiopure (R) and (S)-α-trifluoromethylalanine containing dipeptide building blocks ready to use for solid phase peptide synthesis

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Boron-Zinc Exchange in The Diastereoselective Arylation of Sugar-Based Aldehydes: Stereoselective Synthesis of (+)-7-epi-Goniofufurone and Analogues