Synthesis of nucleosides. 10. General synthesis of N-glycosides. II. Synthesis of 6-methyluridines

Niedballa, Ulrich; Vorbrüggen, Helmut

doi:10.1021/jo00939a009

Cited by 115 publications

(10 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…First, ethynylation at position 5 of 7 proceeded successfully when treated with trimethylsilylacetylene under basic conditions; subsequent methanolisis produced the desired ethynyl product 8 . After removal of the isopropylidene protecting group of 8 and subsequent acylation of the resulting hydroxy groups, Vorbrüggen glycosylation of the resulting product ( 9 ) with silylated N 6 ‐benzoyladenine produced the β‐nucleoside 10 stereoselectively . After removal of the acyl, treatment of the resulting product ( 11 ) with (BnO) 2 PN( i Pr) 2 and imidazole triflate followed by oxidation with m ‐CPBA gave the desired protected 2′,3′′,4′′‐trisphosphate 12 .…”

Section: Figurementioning

confidence: 99%

“…Scheme3.Synthesis of 5'-alkynyl-5'-deoxyadenophostin A(4 of the isopropylidene protecting group of 8 and subsequent acylation of the resulting hydroxy groups, [13] Vorbrüggen glycosylation [14] of the resulting product (9)w ith silylated N 6 -benzoyladenine produced the b-nucleoside 10 stereoselectively. [15] After removal of the acyl, treatment of the resulting product (11)w ith (BnO) 2 PN(iPr) 2 and imidazole triflate [16] followed by oxidation with m-CPBA gave the desired protected 2',3'',4''-trisphosphate 12.Finally,the benzyl protecting groups were all removed by BBr 3 treatment [17] in CH 2 Cl 2 at À78 8Ct o furnish the adenophostin unit 4 with an ethynyl group.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Highly Sensitive Measurement of Inositol 1,4,5‐Trisphosphate by Using a New Fluorescent Ligand and Ligand Binding Domain Combination

et al. 2016

View full text Add to dashboard Cite

Based on the results of our previous adenophostin A structure-activity relationship studies, two fluorescent inositol 1,4,5-trisphosphate (IP3 ) receptor ligands, fluorescent adenophostin A (FADA) and fluorescent low-affinity ligand (FLL), were designed. Binding of the fluorescent ligands to the fluorescent IP3 sensor in protein-expressing cells caused FRET. This principle was extended to a cell-free assay system by using the fluorescent IP3 sensor bound to agarose beads. The effect of FLL on the FRET signal was reduced by subsequent addition of IP3 . The IC50 values of IP3 on the FRET signals were 139.7 and 352.1 nm for 30 and 100 nm FLL, respectively. This method allowed quantitative measurement of IP3 concentrations below 10 nm and was applied to measure cytosolic IP3 concentrations in COS-7 cells and to examine the potency of synthesized adenophostin A analogues.

show abstract

Section: Figurementioning

confidence: 99%

mentioning

confidence: 99%

Highly Sensitive Measurement of Inositol 1,4,5‐Trisphosphate by Using a New Fluorescent Ligand and Ligand Binding Domain Combination

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Similarly, with phthalic anhydride it afforded 6-(4-methoxystyryl)-4-(N-phthalimido)-3-(2H)-thioxo-5-(4H)-oxo-1,2,4-triazine (15) (Figure 4). Some glycosides of 1,2,4-triazine have been reported to have biological and medicinal activities [17][18][19][20].…”

mentioning

confidence: 99%

Synthesis, Characterization and Biological Activity of Some 1,2,4‐Triazine Derivatives.

et al. 2005

View full text Add to dashboard Cite

4-Amino-6-methyl-3-(2H)-thioxo-5-(4H)-oxo-1,2,4-triazine (1) was condensed with 2-methyl (or phenyl)-4H-3,1-benzoxazin-4-one (5a,b) in boiling acetic acid to give compounds 8-11. Reacting 1 with chloroacetyl chloride afforded the corresponding chloroacetamido and triazinothiadiazine derivatives 12 and 13. Condensing 2 with succinic anhydride and/or phthalic anhydride yielded compounds 14 and 15. Benzoylation of 4-amino-6-methyl-3-(2H)-thioxo-5-(4H)-oxo-2-(2,3,4,5-tetra-O-acetyl-α-D-glucopyranosyl)-1,2,4-triazine (19) afforded the corresponding 4-N,N-dibenzoyl derivative 20. Deblocking of the N-2 glycoside 21 and the S-glycoside 22 by methanolic ammonia gave compounds 23 and 24. Acetylation of 4-amino glycoside 25a afforded the corresponding 4-mono-and 4-diacetyl derivatives 26 and 27. Deamination of 25a,b yielded compounds 28a,b. Methylation of compound 28b afforded the corresponding N4-and S-methyl derivatives 29 and 30. J. Heterocyclic Chem., 42, 935 (2005).

show abstract

“…This might be related to the fact that the classical condensation method with 6-substituted pyrimidines has almost always resulted in the predominant formation of N~-glycosylated products (12)(13)(14)(15).…”

mentioning

confidence: 99%

“…Concurrent deprotection of 2',3'-0-isopropylidene and the 5'-0-methoxymethyl groups in the above products (4-6 and 8) was accomplished with 50% TFA at room temperature to furnish the corresponding 6-alkynyluridines (11)(12)(13)(14) in good yields. The results are summarized in Table 2.…”

mentioning

confidence: 99%

Synthesis of 6-alkynylated uridines

Tanaka¹,

Haraguchi²,

Koizumi³

et al. 1986

Can. J. Chem.

View full text Add to dashboard Cite

6-Alkynylated uridines, a hitherto unknown class of compounds, were synthesized by a coupling reaction of terminal alkynes with 6-iodo-2′,3′-O-isopropylidene-5′-O-methoxymethyluridine in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide. 6-Ethynyl-2′-deoxyuridine was also prepared by using 6-iodo-3′,5′-O-(tetraisopropyldisiloxan-1,3-diyl)-2′-deoxyuridine as a starting material.

show abstract

Synthesis of nucleosides. 10. General synthesis of N-glycosides. II. Synthesis of 6-methyluridines

Cited by 115 publications

References 9 publications

Highly Sensitive Measurement of Inositol 1,4,5‐Trisphosphate by Using a New Fluorescent Ligand and Ligand Binding Domain Combination

Highly Sensitive Measurement of Inositol 1,4,5‐Trisphosphate by Using a New Fluorescent Ligand and Ligand Binding Domain Combination

Synthesis, Characterization and Biological Activity of Some 1,2,4‐Triazine Derivatives.

Synthesis of 6-alkynylated uridines

Contact Info

Product

Resources

About